NY hunter,
For the last 20 years I have been using, special interest cars as daily drivers / company cars all, except a Citroen DS 21, have been convertibles
Currently I have a 64 Cutlass convertible as a daily driver/company car. It has a 455 out of a 72 Olds 88, a 200R tranny, out of a Buick Grand National, posi rear end and gets 16 MPG with a 750 carb. I visit my accounts 3 times a year in it, KC to Denver, Denver to El Paso, El Paso to OK City, and Tulsa, then to St. Louis and back to KC. Kids and I went to Chicago and then LA doing a route 66 cruise and to Williamsburg over the summer.
Prior to that ran a 66 Galaxie 500 convertible for 2 years as a daily driver.
I have found buying one with the body ready works best for me, as the mechanicals on these old cars is more grunt work then artistry. Also find it smart to convert to disc brakes, up front, and HEI. I will drive these until it is bodywork time and then sell them, always for more than I paid for them. If the top goes down the price wont.
I too like Chevy, but have found that I can get a sister model in an Olds or Buick, with easy parts interchange, except on some trim items, for several thousand less.
For what crate motors go for, it may be cheaper to buy it built, then to build it.
I have a craving for fins now or something pre-war. Casually looking for a 59 Electra convertible with a straight body and interior and no running gear, or a Ford cabriolet or even a Packard 120, sub frame it with a C-5 Vette front and rear end, add a 350 or 502 stroker crate motor, and viola, fun ride and dependable. Good luck and have fun.
Life is no joke but funny things happen
jon