In exchange you will do your best to get it rented quickly and minimize disruptions with showings. 

You have all the control.You could stay in your own Vacation rental for free for a period of time (add this to your agreement)Make sure of their abilities, don't rent to someone that this is their first attempt at a STR.You have little risk in this scenario.Get first, last months and a security deposit to further minimize your risk and screen them like you would a normal tenant.

Will depreciation help minimize cost if SFR is break even or not cash flowing?

It doesn't help that glyphosate really does work like magic where it's used in the public eye, a solution to clearing residential weeds with minimal proven short and long-term negatives, too, far safer for children and pets than anything else ever used.

I'm inclined to start with all cash on my first purchase for two reasons: 1) minimize risk (if rehab takes longer than expected, or getting tenant takes longer than expected, I'm not paying the mortgage) 2) move quicker on a deal, without having to wait for financing The good news is you can still refi your cash purchase and pull all/most of the money out (if the deal is right), so you can then scale quicker if you're ready. 

From a macro purposes, the population is declining and job growth is minimal.

Seems like bad form if you spent time pitching a seller on the benefits of seller financing only to refinance the deal and the bank pays off the balance of the note all at once.

This minimizes the amount of money taken out of your income for taxes.It may be better to create an LLC before you buy a rental property so you can avoid having to notify your mortgage holder that you are transferring your title to the LLC, in which case they may choose to close the loan and issue you a new loan.

I've been doing some research and for asbestos you're required to do testing if you're disturbing more than a certain square footage or linear feet, and it's very minimal. 

Should I sell the town home and use the profit towards the new home I plan to buy (550K max) in order to have a lower monthly mortgage payment while renting the basement to have minimal out of pocket mortgage payment.Use the profits to put half towards the new home(550Kmax) and the rest split towards my current home and the single family home to lower the mortgage on both while renting?