Bamboo sticks or a small trellis will help keep it upright. I'm not sure it will make the jump to living outside in Florida weather after being an indoor plant for 4 years but maybe start it out slow and take it outside some days to get it used to the change in temp and sunlight. Maybe keep it in the shade for a few days before slowly introducing it to direct sunlight.

When is the last time you repotted it? Is it growing enough roots to support itself?

If it's too top-heavy, pruning is absolutely the right thing to do. It means the plant will be putting energy into growing the roots and trunk, and less into just growing taller. Pruning is part of regular plant care, not something to avoid. (Also, you can use the cuttings for propagation, either to make more plants or to give/trade).

Also, weird contortions usually mean it's been straining to reach enough light. Is it getting enough? Have you been moving it so that it doesn't lean too far in one direction?

I have nothing of value to add, but I would like to know what the rope did to warrant being censored in the first picture.

I'd rotate it so it starts to grow to the light and give it a bit more balance.

I'd personally try it outside and see his it gets on with the drainage holes, can always bring back in if it gets sad.