I'm looking to purchase my first short term rental in an expensive market and was wondering about how many people are able to manage their own properties even potentially clean, fix them.

Consider all revenue and expenses and calculate best and worst case scenario.

There are other choices and options for lower down payments as well. 

That makes your next purchase less risky due to higher reserves and the ability to earn interest on your cash if you put it in an interest bearing account until you need to use it which will counter the mortgage rate being higher.You will also get a lower payment on a 30 year refinance versus a shot term line of credit usually around 10-15 years on a 9-12% rate versus a 6.75% to 7% with good credit.

People usually estimate about 10% of revenue for cleaning expenses.

He is willing to deduct money off the cost of the building for the needed repairs and just lower the price for me to do the work.  

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. 

They don't mention that they are breaking the law, not paying taxes, not accounting for their expenses, certainly not counting for the time they spend operating it, and more.Luke 14:28-30 Suppose one of you wants to build a tower.

I'm wondering if my market warrants the staging expense.