Now is not the time to be vague.
No crank after it rains..so, if you wash your truck it won't start either?
"will start after everything dries up"..how do you dry everything, and what exactly are you drying?
Does it happen at operating temperature?
Does the truck have to be cold to start again?
The oil issue, is well, an issue..however not causing a stall out scenario.
Further diagnostics to determine if it's a fuel delivery issue, or ignition.
Shooting from the hip, I wouldn't rule out the ignition control module.
Give your mechanic the entire symptons, and when they occur..he being a...
Welcome..cool that you have all of that family history with it.
As for direction/color/etc., be true to yourself.
It's your pickup now, let you come thru in the direction you take.
I wouldn't install one, or high back bucket seats, or a visor, etc. The point I'm trying to make is we all have different taste.
The only one who should care/concern themselves about your mods, are you.
If we all thought alike imagine how boring we all would be.
I'll preface this by saying I'm no professional painter/body man..although I've painted several of my own cars.
I start with 1000 grit, 1200, 1500, 2000, and finish up with 3000 grit, then the buff.
Here's a pic of my '40 I recently did.
I use acrylic urethane from TCP Global.
Welcome.
I'd search out a reputable machine shop in your area, and have your engine rebuilt (long block), using quality parts.
As for doing the work yourself, sounds like you're up for it, so go for it.
Good luck.
Nothing wrong with "spending all this time on a base 3/4 ton".
That's a huge part of the appeal of these trucks..they all have a following/attraction regardless if it's a SWB 1/2, LWB 3/4, 4x4, 1 ton.
Like the attention you're giving a well deserved family heirloom.
Bolting to the extreme forward threaded boss in the head as pointed out is the obvious answer.
As for compatibility/wrong headers, size up/place exhaust manifold gaskets (header gaskets) against the head then the headers, for alignment/fitment. I doubt that is the issue though.
In our "neck of the woods" the price isn't that great.
My reasoning, around here a guy can usually come up with something a bit nicer, needing less, for the difference of less than what it will take to get that one in like/same condition, but without doing the work.
Color combination is a winner...
I understand it can be difficult, but first clean everything you can, the dye is also a good idea, but a clean canvas to identify the origination of the leak is key.
"no backfire"
Without knowing the age of them, and the fact that they could be "20 years old", my guess is they rusted out internally.
A lot of condensation builds up, particularly if truck is used irregularly and/or short trips.
"Holy Grail" label, can be as different to us individually, as the memberships personalities are here.
Highly optioned I'm sure most would agree, command higher prices, therefore more desirable...probably.
Rare combinations doesn't always equate to more interest, or a higher value.
I'm happy if...
Carburetors often get a bad rap..usually the first thing to blame on a poor running engine.
A properly tuned Quadrajet on a 350 can be a wonderful thing, contrary to the general consensus.
Not just GM, but all of the manufacturers overwhelming usage of plastic in the interiors, grilles, emblems, etc. (I get it-cost, light weight, etc.).
Understanding why, doesn't change my opinion on how it cheapens the overall package.