I think this is a calculation a lot of homeowners are making right now--especially if they have a low interest mortgage, equity, and their house will cashflow as a rental.The choice is a personal one of course, but I think your future self will thank you if you pull out some equity from your existing home with a HELOC for the downpayment on the next house and a cushion renting your current home, use a property manager as you have other things to do, and buy the next house and do the same thing again.

I have no personal experience with them but they are the only company I know of that are built more for self managers and small portfolios. 

If millenial homeowners can't even change their home's air filters, or snake a toilet, or change the oil in their car, that's guaranteed future business for HVAC companies, plumbers, mechanics, and those places all need a place to conduct business in.The commercial mortgage pricing software I use has somewhere around 50 different asset classes in it.

The person in the response above who got crushed by a $5000 repair never did have $100-200/mo. cashflow.

The founder appears to have been involved in businesses outside of real estate: ‘My dream is a locally made grooming products business’ | People | nashvillepost.comSo it does not appear there is a lot of track record there, but those are questions I would ask.

You don’t want your lender to go out of business while still holding your construction escrow funds.Can you provide me with the contact info of some recent borrowers?

I don’t know a single person who has regretted owning property here (I’m sure there are some of course, but pretty rare and probably their own fault they didn’t succeed, not the market’s fault).

I have two phones, one for business and one for personal.

@Tim Bergstrom I am a lender with a local bank here in Louisville and an investor personally as well. 

I agree with Andrew’s comments particularly because this is a home you personally lived in and know intimately.