I might have missed the point, is your current 88 a gasser? If so, I highly recommend selling / swapping it for a diesel rig. There are a lot of differences:
Radiator
Oil cooler
Dash cluster and gauges
Air conditioner routing
Front Springs
Fuel tank
Fuel Pickup
Fuel return lines
Fuel Filter
Firewall sound deadening
Entire engine harness
Dual battery setup
Transmission torque converter? I’m not sure about that?
Transmission control (no vacuum on diesel)
Hydro boost brakes and power steering (no vacuum on diesel)
Starter
Exhaust pipes and maybe routing
Convert 6.2 to 6.5 or add turbo = easy
Convert SBC to either = doable but less fun
My current truck is a gasser, and has dual batteries. because it's EFI, it has a fuel supply and return already as well. I will need to change the sending unit in the tank for a diesel sender, or use the TBI pump as a lift pump. of the things you list, the only one that I don't feel like messing with is hydroboost, mainly because I just redid the brakes. all that being said, I am keeping my eyes out for a replacement for this truck, the body is pretty rough from getting sideswiped by a drunk a few weeks ago. I do plan to stick with a Suburban, either a 1987-91, or a 1967-1972 GMC Suburban