I'm in the same boat and it gets crazier every day.  I guess the most important part I would mention right now is complete honesty.

You say "to be with"...

I am not sure what that means, so I am assuming not marriage.

Make certain that the two of you have a mutually agreed set of expectations regarding such financial matters as:

Who pay what bills?
How are such items as insurance including: health, life, fire and casualty and auto are allocated and paid for?
How is ownership of jointly acquired property maintained?
Is it clear that property acquired prior to the arrangement remains with the respective partner?

Dissolution of your living arrangement.  You have to consider that by giving up the hobby, you are probably giving up some of your peak earnings potential for the future.  How are your financial interests protected during and after the arrangement?  

If you are relying upon his(?) earnings during your arrangement, what happens if he dies suddenly?  

Sorry to sound like a downer, but you are making two decisions.  The first is that you want to be with this person and the second is to give up a source of income.  By necessity, you cannot know in advance how the first will work out.  You should do all that you can regarding the second to protect your interests.

Best of luck to you

. . . I don't mean it to be.  One thing to keep in mind is his track record for fidelity might be suspect.  However, what the hell do I know?  Best wishes.

Rushing into anything without a well thought out plan, particularly when it comes to financial matters, could easily lead to this not working out.

If it feels right, go for it..  Not sure about complete honesty up front, however.  What is in the past is in the past, once you move forward.  Neither my wife nor I have ever once had the desire to talk about former sexual encounters..  That leads to nothing but trouble and is all in the past anyway.  Just be loyal and honest in your relationship with him and things will work out if you guys are meant to be together..  Congratulations, love is more important than any of this other stuff in life.  Especially making money, trust me.  Not bragging, but let's just say my income affords me many luxuries.  I lost my wife recently and I can tell you from my perspective not to base your decision either way based on $.  You may get some short term satisfaction with money and material items, but you're better off finding the right person for you in my opinion

Make sure you are going to be taken care of it doesn't work out.
Be smart...think with the big head!
And all the best.  We all are looking for true connection and who knows where we find it.
xoClair