Why won't people in this position consider a small syndicate?
You're probably not flying enough to warrant your own aircraft.
I may have a slightly different requirement to yourself, but I have recently joined an Extra 300 syndicate, with one businessman who looks after the books (very well I might add) and another Ex airline captain, with 15,000Hrs across 50 types and heaps of instructor experience. I have the best of both worlds and hardly have to fret about any of the following issues:
Unforseen maintenance costs (our monthly cost includes a sinking fund to cover any insurance excess or big breakages)
Paperwork that needs doing - we all keep up on this
Hangarage - (again it comes out of my monthly payment)
Expected maintenance - annuals, 50hrs etc. - (yet again it comes out of my monthly payment)
Insurance - (Guess what? - Montly payment covers this)
My own currency on type (It is a high performance tailwheel aircraft and you need to be on your toes. Very available instructor)
I can't imagine doing this on my own, and I certainly couldn't afford it on my own.