We plan to use the home currently for about maybe 2 months out the year and would like to rent it out the remainder of the year on Short term rental.

If I'm already going to be having to fix a lot of the main living area drywall, flooring, and balcony tiling, should I consider options to “enhance” while I’m at it to make the expense more worth it?

The property would cash flow ~$100 a month after all expenses. 

Plan to start small, buy a condo or townhouse wholesale that only needs cosmetic upgrades i.e paint, carpet etc.

I can plan for this if the tenant gives me a heads up ahead of time — which they usually do — but it's annoying.

Like Jimmy says, 'If you think education is expensive, try ignorance'I'll at least go for the Invest In Debt book for now. 

So he does not plan on moving out anymore and will stay until the remainder of his lease.

Once the plan is in place, which admittedly might take some time, they will pull your money (usually plus a bit more the eat away at the past-due amount) from the debtor's paycheck and the court will send the money to you.

After all the planning it’s going to be 13 units total,One 4plex and three 3plexes

Builders are throttling with no plans to ever change that, EVER.