As for when to call in a contractor, it really depends on the scope of work and your comfort level with DIY projects.

I live in southern Ontario in Canada, and here if a tenant doesnt pay the water bill it goes onto the landlords taxes.

My wonderful wife is a Nurse Practitioner, and we live in Katonah, NY.

I am closing on a house and family member of the owner is living there, who has no lease, or should be in the house once I close.

I want to build a home for my family to live in and enjoy. 

The income and price have uncoupled from each other over many years.Similar story in BC, but Vancouver has a lot of foreign capital so income is less of a factor.I live in AB and we saw a huge run up in price because Ontario and BC folks came with significant capital.

If you are open to moving close by your future investment property, I would start by deciding on states\regions that you are comfortable moving to. 

That's the only way this works comfortably.

You live in it for 2 out of 5 years and Sell for up to $250,000 Tax-free.

(I do not live in Orlando, my retired father does)... and my father takes care of all the maintenance (repairs, hiring contractors for electrical, HVAC, roofing, etc.) as well as showing the property for leases, he is my hands and eyes there... all for free, I do not pay him a salary or any compensation, and he does not want one.