I can also allow a tenant to grow with me - just moved a family from a two bedroom to a three bedroom apartment.Personally the only reasons I would choose to invest in multiple markets is a) because I wanted an excuse to go somewhere regularly or b) for economic/geographic diversity.I had the advantage that my home market was good.

I am currently in the market to purchase a tri-plex with the plan to live in one unit, make upgrades, and rent the other two out.

I do have two really good mentors / coaches I work with that would be able to provide more input but they do charge for their time.

Quote from @Kash Tacke: Hi,I have two single family houses in Detroit currently rented out. 

With pulling out your equity (or selling), you can diversify and buy more.I did sell one of my places and used that money to buy two others. 

Four of the DSTs are student housing in Reno, Austin, Alabama and Louisiana and two are apartments in San Diego and Houston.

The IRS is very clear about the distinction between the two scenarios.  1099 subcontractors provide their own tools, set their own schedules are not directed by the hour. 

I do long-term room rentals (min 1 month lease).

Security Deposit: 2600Lease states no smoking/painting walls/no hanging things on wallsTenants have moved out and have left two truck loads of garbage to be removed.Damaged doorPainted walls which got on the ceiling and trim Lots of holes on the walls throughout the houseDamage from windows being left open constantly Weed was clearly smoked in the house (smell throughout the place) so we need to deep cleanWater bill wasn't paid so I had to turn back on utilityMissing keyQuoted costs:$450 junk removal (some furniture)$935 for damaged doors/windows, painting cleaning$30 for utility turn onTenants were only there for a year before moving out so a lot of this is beyond normal wear and tear. 

Some more than others. two units had wood floors that we kept.