I think where you will be questioned the most is on the new purchase transaction since you have owned your current home for under 12 months.

Bonus question: Should I execute the leases under the business name and tenant’s name, or should the leases be in my personal name and the tenant’s name, considering the loan is in my name?

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Currently under contract for one in Sevierville, TN. 

Get it under contract to close in 6-12 months when it is done.

From my understanding, insurance won’t cover a dead tree falling as this is a result of “neglect” but would my current dwellings insurance cover it under personal liability?

Also <most times> adding a extra bedroom but not adding sq ft doesn’t help much on ARV specially currently being under 1,500sq ft.

We are under contract on another right now, but it's an appreciation play.

ya I dont know for sure.. kind of lost touch when Peer st went under.. there is another one like peer st.. 

This is only if I know or have studied under this person (*************, Ron Legrand  ect..).