well back to the issue at hand..... is retapping the nut & using a bigger bolt the answer?
Sure, that would be cheap and will probably work.
The real question is why? Are you in a cold area where you need the hardtop full-time?
I think every new 1st Gen owner goes through the same progression..... you get a truck with a fiberglass top (probably double-wall), then dream about replacing it with a nice single-wall version so that the bolts are easier to deal with on the bedrail, and you can have cool interior dome lights.
Then there's the reality that there's about $500 worth of seals that need replacing to make it seal worth a damn (and usually not even then.....there's a good reason why the front cab corners are always rotten in these trucks!).
Maybe you get that far and get the top working right (and don't have to locate a blown-out hatch replacment (rarer than hen's teeth)....so now you've got a great convertible truck that's......actually completely closed-in.

...... and noisy to drive.....and hot and stuffy in the summer since the back glass doesn't roll down like it does on the later trucks.
So, then the decision is to store the top in the summer to really maximize the enjoyment of the open-top truck. Maybe build a "Greg72 Pulleys From Hell" setup in your garage and store that 350Lb monster as high as you can and hope it doesn't fall and kill somebody in the meantime.
Eventually, the thought of driving with that stupid hardtop installed becomes so offensive that you decide to buy a soft top instead so that you can easily swap between weather protection and sunshine..... the hardtop sits in the rafters (or out behind the garage) collecting spiders and other critters, because you're convinced that keeping the truck "original" will add value someday. Eventually, after about 5 years on CK5 and other internet sites you realize that it's pretty darned easy to find a hardtop if you want one because everyone else is getting sick of storing theirs also.....
You try to sell your top (hopefully it's a single-wall) and find that nobody is interested even if it's almost free... one day, in a fit of frustration you finally take out the Sawzall with a demolition blade and cut the top into small chunks that will fit in the garbage pail and throw it away a little bit each week until you are finally free of the albatross once and for all.....
Disclaimer: This is all speculation, and not based on any direct personal experience.
-G