I had a similar situation as well, though I did stay there for 3 months, I am really glad I did and things worked out well, we were at that point though, where it was make or break time, we had visited back and forth several times each.
Every single time before I went over there we would manage to get in spats, it is a nervous situation especially if you are going over for a lengthy time and men worry over money I think it's just how it is.
I don't know your situation and only you and he can judge how you feel about each other. It wouldn't hurt to make sure that the time frame and the finances are what is appropriate.
I will say this though, it has been a long ass slog for both my DF and I , more than once through the 7+ years we have been going through this we broke up, but we could never manage to stay away. Right now I am 100% positive that we will last til we are both doddering and grey.
LDR's are freaking HARD!!! hard hard hard, no two ways about it.
My DF and I had a similar thing, he wanted me to work and get money to make trips etc, but hated never seeing me, he has the same feelings, it's my money and he can't tell me what to do with it. As far as how long to stay we went back and forth on that eventually I just had to set a time frame and he said fine.
If this is your first time meeting each other, I think it is too long, if it isn't... then it may be fine.
I am not much the jealous kind and my DF's personality is such that I never suspected him of cheating, but I got the other end of that. I have a lot of guy friends and I don't keep them secret but I had to put up with grief!!! If you can't trust him... that could be a problem even if it is you and not him. If it's the other way around and you really think he is faithfully challenged that could definitely be a problem.
I can give you understanding and let you know you are not the only person going through this. As far as advice goes tho, I think that the situation is something you have to trust your gut on, as well as your head... sometimes the heart can get in the way of making rational decisions, and your boyfriends difficulty with input could be insecurity or a myriad of other issues... you will have to find a way to approach the subject that will not turn into an argument. Remember the I feel's and the I think's and I really want to know what you think about this and just make sure not to say you you you, ya don't want him on the defensive.