Currently I’m operating it as a STR, but I need a new cleaner and the quotes I’m getting are in some cases double my nightly rate, and the amount it grosses is only slightly more than what it will do as a LTR.

Almost always, vacuum cleaners.

Tenants leave the 15th and I plan to patch holes that evening and paint + hire cleaner on the 16th and have new tenants move in the 17th. 

Run the numbers, check for cleaners and handy people availability, see what you can find to outfit the place locally, etc etc.You can, even today, still score a deal and do well with a STR.

This is something that can be managed with the right dynamic pricing software.Question 2 - No the cleaner should be able to act as the Resident Agent as long as they are comfortable with the responsibility.Hope that helps! 

Can your cleaners handle more workload such as adding revenue generating packages?

You will need to get a photographer, easy to do, just call a realtor in the area and they will have contacts for that.You will need to get a new cleaner.

@Cody M.I would add a Phase I Environmental Site Assessment as a contingency to any offers on properties more susceptible to environmental issues (dry cleaners, gas stations, auto repair garages, etc.)

Transparency always wins.3)Make sure to have mattress and pillow protectors, top-notch cleaners that take pictures of every sheet as they lay it before guests get there, and consistent pest control.

Our cleaner says she has another house on the lake that does Fri-Fri and fills the whole summer...unfortunately (or fortunately) there aren't a lot of other STR large lake houses around for us to comp.