The only reason zillow is even remotely close on their estimates is because they pull in MLS feeds.Do yourself a favor and find a good, investor real estate agent and pay him/her to do your property evaluations.

I'm under the impression that having worked for 24 years within the secondary market for Life Insurance policies (Life Settlements), coupled with 17 years in residential real estate (from property management to rentals and sales), I will find the learning curve on this easier than most.Please tell: do you, Emmett and others, think this is a fair initial evaluation?

They can better assist you in calculating exit prices, evaluating past, current, and the potential near future conditions which is important for a flipper.As to the reimbursement, they should get most of your listings on the exit.

I recently spoke to my realtor, who stated there are several appraisers in my small town and they continually have different ideas of evaluating properties.

do you keep a tenant issues log?

Be able to simply and clearly articulate your business plan/investment approach and ask "Would you be interested in evaluating these opportunities as I put them together?" 

As such, I have been evaluating keeping the current residence as a rental property.  

Confirm everything and build your own model that is based on your cost base to understand how much you can pay for the property to cash flow appropriately for you.For starters, there's some great templates on the BP FilePlace for evaluating apartment complexes.Short list of things to think about / budget for (outside of taxes & insurance of course):-Plan on at least 5% vacancy.  7-8% if you want to be conservative-Are you going to manage it or outsource?

Like @William Hochstedler mentioned though, evaluation isn't based on income for less than 4 units.

I have been evaluating these companies, as well.