you are likely to get a lot of different ideas or thoughts on your many questions.

First I have to assume you are single? No mention of that, but seems you would have to be to even consider this arrangement. And you travel a lot.

Would there become a time while traveling a lot that the itch comes anew that you want variety for spice again? That could put a hurt on most agreements.

Rule? Wow, I doubt that anyone could provide rules for you that you and your selected lady should be coming up with yourselves. Lot of things that would come up later I am sure that were never thought of no matter how much you try and cover all bases.

Retire/work? Speaking only for myself and that this is certainly a LTR, I would have nothing of her working on the side, especially if I am paying for everything. Actually, I thought of this concept in small measure a ways back when traveling a lot myself. But, it was not in LTR terms. It would have been 3-4-5 days a month. Then having thought about it more, figured that was not going to happen, not with me anyway.

Prepare for the unknown I guess, since there will no doubt be a lot of that mentioned above.

Good luck with a contract on this deal. Although there are some lawyers out there that would not bat an eye to bleed you both dry, for what you both could have done yourself by honest disclosure and expectations. But a contract, I kind of doubt it. Funny though I can imagine what the host of rules would be that were demanded on both sides. Yikes.

Not sure this helped much at all, but it is an interested proposition you are posing for advise. Best of luck to you.

I think you need to talk it over....

...with the lady you're thinking about having the LTR with...her rules are the only ones that will matter.  Brooke gave you the best advise, and  her advise works for any business situation....know what you want out of the deal, and can you deal with the downside...the good stuff takes care of itself.

What concerns me, and is what motivatd me to post, are the questions you asked...with the exception of #5, you seem very naive...and I don't mean to sound critical, we are all naive on one thing or another, but this is not the type of deal or arrangement that is taught...I could be wrong, but I believe you have to know these answers in your own mind first & then seek confirmation.  

Let me ask these questions of you...what do your instinct tell you? And if you lost all your money in the deal, would it be a set back?

I don't know if I'm any help...and what you asked is not much different the the behavior in someone asking business start up question. But my instinct, from your questions, tell me you should work for someone in the field first...but in this case, how do you do that? Good luck

I suggest you

I suggest you to look for a sugar baby not a provider, cost wise you will be better off.