I hear that. It is ball-sweatin' hot.

That makes guder sense. PO was at least wise enough to realize that his hi-po alternator might could start him a nice mallow-roasting fire up under the dash sometime, hence the ammeter bypass. You should be okay with hooking your gauge to an off the shelf O'wrongleez 10si. Probably 61 amp max output. Ammeters were a great match for old school generators...I'm talking pre-1965 charging systems. As generators became obsolete and got replaced by alternators, which are wound much differently BTW, ammeters were a hold over form of measurement that still worked fairly well for low amp output alternators. As time went on, cars got more sophisticated, electrical demands increased and alternator outputs had to increase in kind. That's when ammeters began to show their dark side. As you are now aware, the entire electrical load must pass across both ammeter terminals, inside the cabin, via a very long and relatively small gauge wire, before getting back to the battery. All domestic automakers did it this way for a time. GM and FoMoCo realized the downside of this combo early on and switched to voltmeter gauges for charging system measurement. Mopar and IHC instead chose to maintain the status quo. IH stuck with it through end of production in late 1980 and Mopar stuck with it well into the 80's, which is crazy to think about. Lot's of stranded motorists in 80's era Mopar products were left shaking their heads and reaching for fire extinguishers.
Voltmeter gauges are much more simpatico with alternators, especially when you start talking about max outputs approaching 100 amps and beyond. A voltmeter is essentially just an accessory that is connected to switched voltage. It does not have the entire electrical system load passing across it. With your truck having the individual round gauges, it would be easy for you to ditch your ammeter in favor of an aftermarket voltmeter. True, the gauge face would not match your other gauges, but...cue the vibrating, spittle-laced tongue/raspberry sound effect. Obviously I'm unapologetically biased against ammeters in favor of voltmeters. I recently went through a charging system failure in my '74 Scout in which the perfectly functional ammeter gauge gave me exactly zero, zip, zilch, nada, nunca indication that I had a problem. The warning I got was from the lights getting progressively more dim, the radio wigging out and the engine stumble-bumbling along because I was running off a battery that wasn't being replenished by the alternator. A voltmeter gauge would have indicated this issue well before any of those devices began shutting down. Don't take my word for it though. Check out websites like Madelectrical and others that do a far better job of explaining the situation than I ever could.
Now, to your starter cranking process when the truck has sat for awhile...You should try to limit your cranking intervals to no more than 15 second bursts at a time, with plenty of pedal pumping in between as you pause the starter. Less is more. A little trick you can do when the situation allows, is to prime the carb from above with a small amount of clean gas poured in. That should light the engine off right away. Now, it may not stay running that first time. You might have to lather, rinse, repeat, but that will get the engine running much faster with a minimum of starter cranking, which is the goal. Why is this happening? Your fuel pump isn't holding pressure, so the fuel drains back to the tank. Its a common issue with mechanical fuel pumps, unfortunately. How have people dealt with it? Several ways. One is to rig an auxiliary electric fuel pump back near the tank on a momentary switch just to prime the fuel line in advance of starter cranking. Another method involves installing a check or one-way valve in the fuel line between the mech pump and the carb. That prevents the carb fuel bowl contents from draining back into the tank. I like this option. Lots for you to digest here. Hopefully you can do it in climatized comfort.