@Ben KirchnerI'm in the middle of this transition - I have actually modeled my investment strategy exactly like the game of Monopoly - I spent the first several years acquiring property - I would buy everything I could ... that started out with lower end, cheaper properties - then I moved up in class and sold some of my lower end stuff .... currently I'm selling several to move capital to apartment syndications - I plan to "observe" the apartment business and learn the ropes (a different world from single family) while investing in syndications - then buy one of my own... but I may just keep my money flowing into syndications in the future... the passive aspect seems pretty attractive.Good luck and Happy Investing,

Get to know every aspect of buying, rehabbing and renting out.

Except I do enjoy the marketing aspect, just not a big type-A outbound phone sales guy.  

I guess the real money comes from the so called living for free aspect where im no longer paying $800 in rent for my current apartment and move out to another property with another VA loan after I refinance next year. from other house hacker experience would you other hackers say its common for a bare minimum cash flow until you move to the next property.

Is that stuff that most PMs don't actually handle, or is it more that most don't handle that aspect very well?

So it can be good to buy a place for the enjoyment aspect of it, its just not a good investment.

@Jonathan New hit the nail on the head in every aspect of his response!

Really happy to have found one site that addresses so many aspects of my new venture!

The biggest challenge so far has been finding great people for various aspects of managing the property.

This part is getting me all mixed up when I think about how to manage that aspect of owning multiple properties.