Biplane
I totally agree with you, you seems to be older and wiser than me, but (always the but) some lessons have to be learned the hard way.
A lot of people told me I did not have enough stick time to get a biplane, and probably because they can not handle it (they been flying more time than I do) doesn't mean I can not handle it either.
I have fly HOG BIPE, Ultimate, Pitts, Stearman, and some are great planes to fly and some keep me in my toes and my legs shaking for a while after landing; but I enjoy them all, biplane freak I guess.
Money is and issue, no doubt, but you should never put in the air something you can not afford to lose. I do a lot of pre-fly checks but accidents happens or you just push it to the wrong side; expensive but all valuable lessons.