For example would you fly on a plane with a first time pilot for $100 flight or with someone who has been doing it for 30 years for $300....

If you stick with one method, as soon as the market changes, you will have a severe lack of inventory.

Has anyone actually started one of these?

I've been a landlord for a little over 2 years and I've learned a lot of stuff, but one of the most annoying lesson's I'm dealing with is that I just can't trust anything tenants say.

Transparency, I thought I would never be able to afford Alexandria either.We showed up to Old Town Alexandria and started renting. 4 months later we found an affordable house in Woodbridge we could get into for a year with low down, then rent it, in the mean time we recoup the capital from our other 2 properties to go buy again after that 12 months.

Offer the main house as a STR (we would stay in other parts of the property at times if needed). 

Ideally, you would want one that would share systems with you (spreadsheets, budget tracking, walkthrough checklists, etc) this would save you a ton in time and duplicated effort. 

I've been considering a property near one of my kid's colleges that is  currently a multifamily. 3 units: 2/1, 1/1, 1/1.

TIME is money.

I have tried multiple times to get a response, all the way up to the VP!