We have been looking at AirBNBs and VRBOs bookings as well as looking into master host services that can manage the property for us.We need first of all to locate a property (I have been thinking of a 2br, 2ba) as it seems to be easily rentable in the area.

Property Management of long term rentals takes very little time and someone with an extremely demanding w2 can still easily handle managing several units.If you are in tune with your market, you can likely get better/higher rents on your units than property managers would.

If an owner is that easily swayed, you could probably just sell the idea verbally.

I currently have a tenant who's probably in the top 1% of earners in his age group--he has a six figure salary and could easily qualify for a mortgage--I asked him why he was renting from me, and he said "the market's too hot right now--I don't want to pay $700k for a house that I think is only worth $400k"And as others have mentioned, there are many reasons why some tenants might prefer to rent a single fam home over a multifam property, and these issues are often market-specific...Having said all that, there are definitely advantages to multifam properties (they tend to cashflow better, for instance)...everything comes with pros and cons...At the end of the day, it all comes down to whether the numbers make sense--which is why it's critical to know how to analyze properties & markets.Good luck out there!

For now everything is great, I just find another house in one of the best neighborhood in Richmond VA, Mechanicsville, a house 3 bed and 2 bath, easily you can rent it out for 1800, plus there are a guest house very separated from main house, fully equipped, 3 bed, 1 bath, 2 living room and kitchen , separated entrance for another street, and parking space for more than 2 cars.

At least one will give you the impression that these are minor problems compared to what they are used to and will be able to handle it easily. 

I'd maybe model out a possibility of having a few units as STRs that can easily convert to LTRs, but wouldn't rely on it. 

(obviously, no; a beginner could easily get themselves killed on double black diamond terrain!).

Finding buyers for a lot is like trying to find a needle in the haystack, plus someone buying a lot seems to have less urgency than someone buying a house, so they are prone to fall out of escrow more easily.

This would allow me to easily split the living areas and provide an "entire space" to list on Airbnb as most travelers do not want to share breakfast with their host!