Talk to some sales people and advisors from a payroll service such as Intuit or ADP, etc...

I would have paid another experienced local investor (an unbiased party not having anything to do with the sale of the home or selling me services) to do a thorough video tour of every inch of the house before submitting an offer. 

Bought them both on short sale in 2017 and 2018 and have no issues keeping them rented.

I have been assured by the lender that there will be no due on sale enforcement. 

I don't know the cost of things in your area but you would get the proceeds of the sale tax free from federal income tax from the primary residence exclusion.

Starting from scratch with power poles, septic tanks, roads, drives, etc. 

You sign the Purchase and Sale agreement with the seller.

Realtors are not one of my favorite middlemen on the sale side either.

Timing of the sale of each might be an issue, it's a complicated strategy you will want to think through and plan for before you list either property. 

- My friend has a whole sale account for printing mailers for an excellent price however, I would have to mail them somehow.