a number of years ago, I was fortunate enough to realise a dream and get a proper classic car, something I'd always wanted to do from when I was 17 running an old 1972 mini from necessity and reading practical classics.
I looked at the cars I wanted then worried about price without being silly to start with. Then spent ages researching what I was thinking and then tried some including just hiring one to convince the Mrs. Then narrowed down the model and compromised on price / spec to get to something that I could justify and afford.
My point is, as per previous comments I would start with what have you always wanted, this is a reward for hard work per the original post, the search is part of the fun, I would definitely try some to see how you like them then think about budget and what can be afforded.
what you could do which may be of interest to others (well me at least) is post some pics of possible candidates like the Marin FRS to see what people think, I always loved the idea of titanium full suspension but not many left uncracked and no idea what they cost.