A 'project' is a 'project'. Nobody ever re-coupes (pun intended) their money unless they finish the project. Changing the car from point A to point B would likely mean the selling cost is the same, even though you spent $$ getting from point A to B.
An actual driveable car will always be worth a bit more. So I'd focus your energy (and $$) in that direction. And it has been proven many times that the more 'original' the car is, the more it will be worth. So if you are not in it for the long run, your money is probably better off sitiing in a 1% savings account. If you plan to keep the car for 20-30 years, you will likely (finally) be able to sell the car for more than you have into it.
Ususal rust areas are the rear shock towers (as viewed from the trunk), around the window edges, under the cowls, rear and front wheel wells, frame mounts, lower render areas, bottom of doors and jambs. These cars attract rust like nothing else!
The most dreaded part is spending three to five years doing 'something' to the car, then losing interest, then selling for a loss. The amount of sheet metal work required can be staggering. (see the other thread about the 'vert project that has been updated lately, or look at the resto of my '67 on my photobucket) My '67 was done by pros. I thought I knew a lot about bodywork, but that car would have been way out of my league. But I absolutely love it now and will likely hold onto it for 20-30 years. I just picked up a numbers matching '68-400 coupe for less than your number, so use those pictures to compare. I lucked out with the car still retaining the original drivetrain. It will be going a similar route as my '67 soon.
And if you cringe at the $65 PHS cost, I think you should re-think your investment already. You need to be able to hold $500 cash in your hand and then light it with a match. That's what it's going to feel like working on these cars. Others here can throw their 2 cent descriptions here too, but in the end, it has to be a labor of love for fgf's, not an investment.
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