I feel your pain. These old cars take a lot of TLC and maintenence to keep them running well. And yes, lots of $$.
Just pretend you live in the upper midwest. Most of us have our cars tucked away for winter, and can't wait for spring when it will all be new again. (one could argue either way)
It will all work out. I'd recommend you check out some local car shows and start asking around about good mechanics. I was able to get the name of 'a friend of a friend of a friend' years ago and now can consider him 'my friend' after working on my cars a lot. He has done all of my E/T rebuilds, and after five years I've only had one small issue with something he did (which he fixed right away). So there are good people out there, you just need to find them via word of mouth.
I used to be indecisive. Now I'm not sure. I feel like I am diagonally parked in a parallel universe. 1968 400 convertible (Scarlet) 1976 T/A - 455 LE (No Burt) 1976 T/A New baby, starting full restoration. 1968 350 - 4 speed 'vert - 400 clone (the Beast!) 1968 350 convertible - Wife's car now- 400 clone (Aleutian Blue) (Blue Angel) 2008 Durango - DD 2008 GXP - New one from NH is AWESOME! 2017 Durango Citadel - Modern is nice! HEMI is amazing! 1998 Silverado Z71 - Father-daughter project 1968 400 coupe - R/A clone (Blue Pearl) (sold) 1967 326 convertible - Sold 1980 T/A SE Bandit - Sold