We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

You can use your own funds, use a HELOC or do a cash out refinance to cover the costs.

Sellers may struggle to mentally shift from "owner" to "tenant," which can create challenges with boundaries and property care.Security Deposit:If you’re doing a temporary leaseback, be sure to collect a substantial security deposit to cover potential damages and ensure they vacate on time.

If you generate enough money annually to dismiss a W2, then consider covering the ever increasing costs of retirement & health care and those do not go at inflation metrics but usually way higher. 

The 2 units that are rented are covering the mortgage so yes there's room to lower the price on the other 2.

though; (1) there are tenants in the house on a two year lease (payments are enough to cover mortgage payments), and (2) the Seller wants the option to buy back the property in two years.

Before buying or renting in an unfamiliar neighborhood, you should check the following two sites: SpotCrime, AreaVibes,These sites provide valuable information, including Livability Scores, which cover aspects such as crime rates, employment, health, housing, schools, shopping, and more.well, anything can happen anywhere.

I've not covered everything but just given you a start. 

It depends on where you want to live, income, personality, and other factors.You could buy a large home and rent out the individual rooms to cover expenses, but this comes with problems.

If I use a RMLO service I assume they cover the Dodd Frank and other consumer rules?