I get long term tenants that will take care of the place and the tenants would eventually get a free house just for being good long tern tenants.

Eventually I'd like to continue buying rental properties with a buy&hold strategy after getting my feet wet.Any advice for the situation I've described above?

Either way I feel both can eventually bring me closer to my goal of retiring from my full-time job by 40 (26 now).

Those haven't worked for our current areas but we hope to eventually buy one. 

Eventually as you scale larger you wont be able to manage it all yourself.

Then that spreads out of control and eventually overwhelms our system.

We are also buy and hold investors in single family homes and hope to eventually dip our toe into commercial .

However, as everyone was busy eventually the meetings died off.  

If every property you buy does not, you'll soon run out of money and may eventually become bankrupt. 

Singnificantly easier to partner with an experinced operator and a single asset first and grow towards blind pool later.Your goal is possible...eventually...just reverse engineer what others have done.