So, a tenant caused extension damage to my property.

It gets cleaned after each and every booking ($50), so it's super well maintained, but it's beginning to feel like almost a regular thing that it's drained and refilled ($150).

So, you would want to get something in writing from a lender, to avoid having your loan Note called due for a violation. 

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – so, they often select the first PMC they call or that calls them back!

The next year he would do the same on the 2nd home and continue to do so on the 3rd through 15th and it would repeat back to home #1 after the 15th home. 

I'm looking in a rural place called Cave Junction, OR. 

So partial deduction allowed up to 150kI would be careful giving him a deal on rents as the IRS could classify this as some sort of hobby or non investment property due to not being at or near market rates.

Just had a conversation with a company called Rent To Retirement.

I used to Live in Louisville so, I know Nashville pretty well!  

I'd recommend to first look at where you'd like to invest it to see if it's feasible or if you need to adjust your buying criteria.If you're not in the market for something new then I'd look into adding an ADU on the lot and upgrading the windows on the main unit to triple pane glass so that the noise doesn't bother your future tenants.