Visitors visa and not the "norm" circumstances

Hello everyone, this is my first time posting so please be kind
I have a LOT of questions about obtaining a visitors visa ahead of time(if this is possible) versus taking your chances and just flying over and hoping the IO will let you in. I have some different circumstances that come into play as well. First, some history.
  I met my BF two Christmas' ago while living in Denver, Colorado. At that time we spent 2 weeks together followed up by another 2 weeks the following July. I then moved across country to New Hampshire to live with my mum to save money, work on her farm and be able to go visit my BF for at least 4-5 months. I did do just this in Oct. of last year. This was my first visit to the UK and while I would like to think I was prepared in hindsight I really wasn't. i did bring all my financial statements, a letter from him stating that I was staying with him and all expenses would be paid for by him (except for spending monies) and a two way plane tix. In hindsight I had quit my job in Denver so no work history or leave of absence papers, no real plans (that were in concrete anyways). The IO called my BF and because I didn't lie in the least, our stories matched and I was let in. Now..I think how lucky I was! Some things on my side were perhaps my age (I'm no 20-something) perhaps I'm my Nativity I was confident. It was REALLY hard though to get through to the IO that I understood that a four month visit was not the norm and that would not outstay my visa. As it turned out, I changed my airline tix due to the fact that I did indeed have more time and money to stay. In the end I did stay for the full 6 months.
  My future plans are this right now. My BF will be visiting me here in NH for 2 weeks in September, and I plan on going back this late fall in November for another 4-5 months. Again, a long time for just a visitor. Would it benefit me to apply ahead of time for a visitors visa? I have not been denied entry before so I know there may be a problem with this? It would ease my mind greatly to know ahead of time that it was OK to stay there.
  Now, some of my questions. The reason I have so much time on my hands is due to the fact that I live and work in a resort town. We are busy all spring through fall but then work drops off dramatically. This is when most people in this area travel and to also get away from the bitter cold and snow.I will have a letter from employer stating this and that I am expected to return to work in the spring. My other concern is my living arrangement. I live and work on an organic farm(MY mums farm) and in exchange get free room and board. I am again, expected to be back in the springtime to help out again. Should I have a letter from my mum stating this? I would think this would prove my strong ties to my family and the US. And now a work question. I am also an artist and have some things in a gallery with an ongoing income. Can I show this as part of my income ? Can I also produce my art while I am there or is this considered "working" I also have an on line store that I sell my art on is this allowed while I am there? I am kind of confused about that as i am not really "working there" but as an artist this is a great country for inspiration!!

Another question, my mum would like to come over and visit France with me while I am there. she doesn't have a airline tix right now but how would that work with the visitors visa versus just the 6 month visa stamp. Would her comming to visit  me and traveling together hurt or help my chances if I had to explain this? 
  In the future I would love to settle there permanently, but an wise enough to know to go through the legal and correct channels. I'm hoping that my six month first time stay does not hurt my chances of going back this winter and perhaps for good at some time in the future. Any advise, thoughts, opinions, are greatly appreciated. You all seem very insightful and knowlegable! thanks in advance. 

When exactly did you go over to the UK and when did you leave?  You cannot visit for more than six months in a twelve month period.

I went over in oct of last year and came back in april of this year(from Oct 28th to mid april) almost exactly 6 months in one go.

When exactly did you go over to the UK and when did you leave?  You cannot visit for more than six months in a twelve month period.

Not to be a PITA, but I believe this is a guideline- and not a rule.  I've spent almost eight months in a calender year (this year), and never had a lick of trouble with immigration.  They look at my passport, see my stamps, ask a few questions and wave me through.  I've never produced a bank statement, lease agreement, job info, or even a return ticket.  I always carry these things with me, as a precaution, but have never been asked for any of it. Maybe I'm just lucky. (knocks wood)     

yes, I believe that is is a guildline and not a hard rule, however from my investigation into the matter, any more than 6 months will throw a red flag up that you are trying to settle there avoiding the legal course of action. My goal is to do everything within legal paramiters and in doing so, to strengthen my chances of staying there permanently. BTW I have to say. My being there for the six months was my opportunity to figure out how I would like living in the UK (which, hands down..I absolutely loved it there) and to make sure that my BF and I were compatible ( I love him with every fiber of my being). Don't get me wrong living in the States is OK but  traveling to another country really opens your eyes to so many other possibles and given the fact that I have met someone so dear to me makes it all worth while.

I would apply for a visa in advance. The cost is nominal and it would be more than worth it in my opinion.  You dont NEED it, but your chances of refusal are higher than most b/c of the reasons you mentioned.

Here's a link to the UKY Wiki on Visitors Visas: http://www.uk-yankee.com/wiki-manual/index.php/visiting-the-uk/index should have all the necessary info of where & how to apply.

Thanks WebyJ for the info.
Hello Mirrajay fellow Denverite congrats on your move..looks like you will be in the UK in 7 days !
 Mirrajay, I agree that it would probably be in my best interest to get the visitors visa ahead of time but which circumstances do not go in my favor? The sidetrip to France? The fact that I work in a resort town? All of it makes sense to me as to why I travel this time of year and not really in the summer, I just hope it makes sence to them as well!
..now...if I get denied a six month visitors Visa what are my next steps? I am hopeing for the best but preparing for the worst as you can imagine and want all my bases covered.
  Also can anyone answer my question about still doing my art there? I would possibly be looking for upcoming art shows and the like.

http://www.ukba.homeoffice.gov.uk/visitingtheuk/visitors/eligibility/

come to the United Kingdom as a general visitor you must be able to show that you:

■only want to visit the United Kingdom for up to six months;
■plan to leave the United Kingdom at the end of your visit;
■have enough money to support and accommodate yourself without working, help from public funds or you will be supported and accommodated by relatives or friends;
■do not intend to charge members of the public for services provided or goods received;
■do not intend to study; and
■can meet the cost of the return or onward journey.
■do not intend to carry out business, sport or entertainer visitor activities;
■do not intend to marry or form a civil partnership or give notice of marriage or civil partnership;
■do not intend to receive private medical treatment during your visit , and
■are not in transit to a country outside the Common Travel Area.

If you want to do business during your visit you also have to show that you:

■normally live and work abroad and you have no plans to base yourself in the United Kingdom; and
■do not plan to work, produce goods or provide services in the United Kingdom.

I think you could do your art just as genuine personal art, but you cannot show or sell it whilst here

Yay, go Denver!  woo!  

IMO, which is not a professional one, the thing that works against you is the amount of time you have spent in the UK this year already.  It IS a guideline and people like Sarah have had no trouble at all, but I personally wouldnt risk it.  (I'm a worry-wort though!)
Your immigration history may also work in your favour, though, since you have stayed for long periods and left within the alloted time in the past. Really its all down to the risk you are willing to take.
I dont think the trip to France would be a problem - if anything it shows you are a tourist, which is good.

If you do not apply for the visa in advance, the letter from your employer/mom will be helpful as it shows your ties to the US, which is exactly what they are looking for.  All of what you say makes sense to me too, but you never know how they will view the same thing.

Oh, and you asked about working on your art in the UK - as far as I know, you cannot do ANY kind of work even if its writing, crafts or artwork.

Also, since the visitor entry clearance is for multiple entries, you'll have an easier time getting back into the UK when you return from France.

Re the 6 month spent leave rule...

http://www.londonelegance.com/transpondia/spentleave.shtml

*However* I have been under the impression that this provision was booked for a fundamental change sometime this summer.  I haven't been tracking it because the many consultation responses and all the legislative briefings have been so draining.

The change I was informed about has to do with replacing the 6 out-of 12 constructive rule with a easier to understand 6 months flat rule which is "hard" and displaces a lot of decision-making that has been heretofore in the discretionary zone.  I agreed with this when it was put forward by the way.

If this is already in place, then the thread is out of whack.  And if it is not already in place, let's keep our eyes peeled so that we're not giving out dated info.

Re the 6 month spent leave rule...

http://www.londonelegance.com/transpondia/spentleave.shtml

*However* I have been under the impression that this provision was booked for a fundamental change sometime this summer.  I haven't been tracking it because the many consultation responses and all the legislative briefings have been so draining.

The change I was informed about has to do with replacing the 6 out-of 12 constructive rule with a easier to understand 6 months flat rule which is "hard" and displaces a lot of decision-making that has been heretofore in the discretionary zone.  I agreed with this when it was put forward by the way.

If this is already in place, then the thread is out of whack.  And if it is not already in place, let's keep our eyes peeled so that we're not giving out dated info.

Garry, if they change it to a 6 month flat rule, would that mean as long as you left in between it wouldn't matter how long you stayed out between visits? Wouldn't that give more people a way to work around the rules?

Oh, and you asked about working on your art in the UK - as far as I know, you cannot do ANY kind of work even if its writing, crafts or artwork.

Surely whether you are a professional or an amateur artist, photographer, writer, etc. shouldn't mean you can't write, paint, journal, or take pictures for your own personal reasons while in the UK.

Surely whether you are a professional or an amateur artist, photographer, writer, etc. shouldn't mean you can't write, paint, journal, or take pictures for your own personal reasons while in the UK.

I think it's a bit of a grey area, but my understanding was that anything you created while on UK soil as visitor can not be used for profit, so unless you only plan on giving away what you've created, you probably shouldn't.