Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

I know becoming a part time agent is one way, but where we live in south Florida seems to be overfilled with agents and I don't think its a great fit for us right now. 

However, If you live in a small town or a rural area, you may need to choose somewhere else to start.

I am currently living out of state so I have hired a property management company to handle this task, however, my home is still sitting vacant with very few prospective tenants.

Quote from @Jimmy Rojas: I live in Arizona and homes here are sky high, youd be lucky to get %6 interest rate, I would be a 1st time home buyer, apart from being 1099 employed would Trumps real estate plans benefit the little guys like me? 

You can actually still find deals where I live in the (very) low 5 figures, and in some cases, still in the mid 4 figures.

I never actually went live on the site because of the 15% fee they wanted.

We plan to come back live in it the other 6 months, fix it up more, repeat that process until we can find another deal that makes sense for us. 

I have no reason to stay in Gilbert, other than it's where my family lives currently, so it's nice to be close. 

I am a wholesaler, I live in Memphis but do most of my work in Nashville as a primary market and Texas, Oklahoma, Kansas, Arizona and anywhere else I can find a deal from networking for multifamily and land.