You could possibly quietly get away with the use of that 2nd dwelling on the property as STR....

We also made sure it was extra clean when the next round of tenants came to see it and accomodated showings.With the exception of what Michaela said about accepting too much rent upfront, I wouldn't necessarily rule them out.  

But I do know local managers that rip off out of state investors and such even tried on me but difference is im here locally and handle my own maintenance and such so harder to get away with overcharging me and such. let me make this very clear I do not offer turn key properties or practice unfair business practices as you seem to almost be implying but like described I do see happening nd this is why I question this cause I would like offer quality honesty and integrity where it is lacking .

I see 80% occupancy year round.

Just an all round person that can do cabinet installs and other finish carpentry and maybe light plumbing and electrical? 

John, in working with 20-30 different insurance carriers, I can tell you they are trying to fit a square peg in a round hole.  

Been a while since i played, but there is a lot of business done during and after a round of golf at the bar ( 19th hole ), do you have to learn to play and go play Golf, NO, but it also wouldn't hurt.

I am a little strapped for time with my 9 to 5 but hopefully I can get away some soon!

So far I've done multiple doses of hydrogen peroxide and a few rounds of sanding in between.  

Generally unless you are in a sunny area year round, August to February is a bad time to sell.