You need to know your business inside and out for 2 reasons.First, you want to talk a lot with these experts you’re going to hire in the other markets so you can test their skills and get comfortable that their expertise is at your level or higher.

My Duplex total payment = 1,480 and the lower level pays me 1,200 while I live upstairs.

Next level up is rehabbers who buy and renovate to resale.

Is this true to some level?

My intention is to do a contract for deed/rent to own deal like my mentor does, the reason being that I'd still have his mentorship in the process, great cashflow, and very low level of maintenance as I'll be around a hour away for college.

I have liquidity from the previous business to invest and hopefully kick start this endeavor.Biggest challenge - I don't know this industry, I am coming from a completely opposite industry in the technology field.What I have, I think, in my favor, are colleagues from the RE industry with experience in both traditional RE sales (agent/buy/sell) but also experience in the REI side (one owning about 70+ properties and the other owning about 25 properties, both using their properties for passive cashflow)With an engineering/analytical background, my greatest fear right now is the unknown and I am trying to shore up that experience through reading and listening to others, but as I have already discovered, its like taking a drink from the fire hose - way more knowledge than I can consume in a short period of time.Questions I would pose to anyone interesting in providing some feedback -- Best way to look for that first opportunity?  

In the end, I never had to move or sell my house, I kept most of the rental property (for some reason she didn't think they were worth much or didn't want to deal with them), and was used to living on almost nothing, so once it was all over, it was like all of a sudden having a large amount in extra cash each month because it wasn't being spent immediately upon hitting the bank account. as a result of maintaining a level headed relationship with my ex however, we didn't need to liquidate or sell the business we still have (as our lawyers were trying to convince us to do)... hopefully in the end things will become very good for you also.   

I make my living talking on the phone, which is my comfort level. 

In your opinion, what level accuracy do you expect when it comes to estimating repairs? 

I would imagine that these folks have a high level of motivation.