If these issues are determined not to be issues, your PM needs to set expectations with the tenant.

Lake Placid has made it almost impossible to break into the STR market.Wilmington (next door to Lake Placid) is also working to regulate the STR market, town is in the early stages of setting the rules.

Complexity also brings about fees - fees to set it up, and fees for annual compliance, and annual registrations for each level.   

I see the $50k you're setting aside within 18 months is for a new home purchase.

It might be affecting availability.To speed things up, chat with your management team, set clear expectations, maybe throw in some bonuses for speedy work, and have a reliable crew on standby for quick fixes.

Investigate what features are most desirable within your target market.

How have you all handled this to set proper expectations with your guests?

You’ll then have a good grasp of how you want your property managed and set better expectations should you still want to outsource.

However, with this opportunity to actually be in Tampa in person we are hoping we can find a market near there that we can make work for us, since being able to visit the home in person will give us an advantage over trying to set up a team and systems without ever really spending time in the market we are investing in.

This would have someone else pay that premium and would allow you to target class b and above areas.