Now Im looking to maximize my potential, gain some financial independence and start making my money work for me and not work for my money.

If the numbers and neighborhood work for me, the age and condition of the property are totally irrelevant. 

For me I think it depends on how much money you have invested into the home and for how long?  

Jeff and I lend our own money and at least for me I do have some investors that I manage their funds along with my own.

Working on figuring out that definition for me and your comments are helpful.  

I googled it and found this:If you rent it to tenants, you would treat it as a rental and report it on a Form Schedule E.

Tools like this helped us determine that retiring in the Memphis Metro area was good for us and has helped form our investing strategy, mainly SFR and some commercial spaces (flex, studios, small office).

To vet guests, you can use a pre-booking form, ask about their plans, and require an ID and signed agreement.

The real work is locating these properties and I've learned the best way to do this is to work in towns/areas that have online GIS systems that map; topography, wetlands, soils, etc. and assessors data available for download either from local sources or listsource.com.  

Im reading a lot right now and this helps me a lot. 2 things I can't understand from properties I've looked until now ( which all requires a lot of work), 1- owners who wants to sell their property and tells me also the rehab price, which makes no sense for me,( even the rehab price for me, with a quick estimation is 30-40% less expensive then told to me. ), 2-  Realtors that don't knows the ARV or rent price after rehab.Thank you again best, Ilir