I'm with most other people here. Don't buy an A36 if your short term goal is to buy a twin...Just explain to him that he may need alot of dual in the plane with a good MEI before he can be proficient enough to solo it. Also talk to him about the possibility of getting his IR in the plane he buys.
I don't read "most other people's" posts to be saying that. I am a firm believer in working up in complexity, as well as the huge dollar savings that would be realized by gaining the instrument rating and meaningful hours in a complex single.
I, too, am what some people would assume is a "rich doctor", but I am also very frugal, as are many doctors. Actually, there are very few truly rich doctors--we are basically smucks, pawns in a system in which we have very little control.. but I digress! I got my private in a rented 172, then flew a friend's 182 for a while until I bought a Cardinal RG, in which I got the instrument rating and accumulated about 900 hours (and lots of educational experience) before moving to a 210.
I can tell you that, in those first few years of flying, it was my routine to go fly at least once a week, to build and maintain skill. Now, with the higher fuel burn of the 210 (and the higher gas prices, of course), I cringe at the thought of going to fly "just to lubricate the engine" and to maintain some level of proficiency. I have to make myself go fly once a month for these purposes and to do a VOR check. My wife doesn't even need to remind me that for every hour that I DON'T fly, we can afford to go out to dinner at a nice restaurant.
I vote for a complex single: Cardinal RG or 210 in the Cessna line, Arrow or Saratoga if Piper (and possibly interested in a Seneca), or Bonanza if thinking ultimately about a Baron. I know that he is eager to take the whole family travelling, but I can tell you from experience that that just doesn't happen all that often, and they might not be all that eager to travel with him until he gains some meaningful experience.
Buy something that you can afford to fly a lot.
Wells