This was brought up in a fairly recent thread. My prior response.
http://www.theeroticreview.com/discussion_boards/viewmsg.asp?MessageID=155433&boardID=21&page=1#155433

For the past 12 years I've almost always had a relatioship with a sugar baby. As you can see from my reviews I've also had a fairly active "independent" life. I like them both. Sugar babies are great to develop a more intimate relationship and independent providers give the variety that every man deserves. I generally see my SB once a week and see a provider once a week.

Re: Sugar Daddy

I did EXACTLY that and my first experience as an SD went sour quickly.

I wanted a bdsm-lite and poly adventure and she didn't really want to be a provider but had very healthy enthusiasm so it seemed like a natural fit.  However, the 3-month experiment quickly turned into one big upsell and it was constant renegotiation while the benefits declined and dwindled.  Simply put, I was treated like a mark throughout.

That said, the effort did have its perks.  I had some exquisite moments and have some outstanding video to help me enjoy the shining moments.  I would do it again [with greater caution] with the right provider(s).

Obviously, ymmv.  I think the trickiest part is escaping the fundamental hourly paradigm and wish you the best of luck if you take the plunge.