Before you spend hundreds of dollars on bags (and make your truck look like the bottom pic) consider a set of RV skid rollers. I fabricated mine, but you can buy them at RV parts houses. Find an inconspicuous mounting spot and they'll roll you right over bumps without damage.
I did bags on my 56 could not get a better ride. You just need to set your wheel alignment at were you want your ride hight
Probably gonna have to do shocks after measuring it I see I only have room for something 5 inches tall and 4 inches wide pretty tight spot with shocks
I think you can get away with a slight raising of your truck in the rear (they look better with a slight rake) and only a taildragger should have the ass sitting below the front. but nothing wrong with a set of helper bags in the rear. I had the same thing on my 53 wagon. Helped me get over alot of stuff.
raising it way out of the question!!! LOL casters would be cool but I found out yesterday driving with my 2 stepsons I was dragging already and I plan on still using this as a move shit around truck plus daily driver sp I need something to help with any extra weight ill have to deal with