Quote from @Collin Hays: I don't manage short-term any more, but can't you include this in a written rental agreement that the guest signs at the time of booking?

This phrase "Are You Leaving Money On The Table" could mean that you may have missed out on money in a deal that was there for the asking.

I would like to buy my first rental property in a few months and am doing some research in order to be as successful as possible.

Property details: 3 bed 2 bath both sides with attached garages, aluminum siding, copper plumbing, 1972 construction, separately metered, all electric water heater, range, dryer, public water and public sewer on a slab foundation in a great school district right next to brand new construction everywhere.

I'm about ready to retire so I'm not looking to compete in a bidding war, mainly looking for a fair deal that I can rehab or a turnkey with some cash flow. 

For me it is not the markets i did not invest in as much as the properties i did not purchase.  

This is especially important if you're on the younger side, as those returns can compound significantly over the next few decades.I'm in a small real estate mastermind group, and we all did this exercise with our own portfolios and identified underperforming properties and equity to reposition, and presented it the group for feedback.

I'm looking at investing in a short term rental in Jacksonville, my budget is fairly modest though, up to $300k so I'm not looking to do a high-end STR.

If this is how it works, do I ever go through the title company like I would in a normal wholesale transaction?

A too high price will translate in a low ROI.