I have not done any long term cruising at this point, just weekend to multi-week trips, but I do plan too and so have been studying these types of issues for a long time. Now, I will not have the unlimited budget "problem", in fact we will need to fall into the extremely frugal cruisers crowd, so perhaps I bias my opinions to make myself feel better but here is one small thing I noticed...
I read a lot of blogs, books, magazine articles, etc of people, most very much better off then me financially who are cruising and one thing I often notice is how often they are waiting around because something broke, Things I do not even have on my boat. (This is just a huge generalization, and not meant to be negative in anyway toward anyone.)
I seem to read a lot of things like "So we are stuck in this port while we wait for X part to get shipped in, and then Y broke, and now we need to wait for three more weeks for the only repair guy to get to it and we really want to get going before the next storm blows in." And often times all the things that are breaking are things I will likely not be able to afford on my boat.
No matter how much money you have, even if you can pay someone to do everything, you still need to wait around for the parts and the people to be available to get the job done. I realize that a LOT of things will break on my old boat as well, but simply put, the fewer systems, the fewer things CAN break.
Of course few systems and smaller boats have huge negatives too. A lot less daily comfort, less room for things, no freezer, so not as fancy of food. I'm not knocking big boats or cool toys, but for me, a big part of the dream of cruising is to get away from the headaches of dealing with way more stuff then I need. Even if I could pay someone to fix it, I would still need to arrange it, wait for the guy to show up, make sure he does a god job, dealing with the effects if he doesn't, etc.
I agree for everyone there is a "sweet spot" to shoot for. I am still young(ish) and can give up a lot more comfort. As with all things in boats, it is a balancing act on a personal scale. But I think I see a lot of people being unhappy when it is not as easy to just throw money at a problem while cruising as it was back home.
Of course, I'll be rowing around to all the big boats looking to bum ice from their freezers, or asking if they got the weather report off their satellite system.