She'll pay me market rate rent, thus keeping that money in the family, and the condo will eventually transition into a more traditional rental property that will support my retirement and that my children will one day inherit. 

Looking to get started soon with an eye on Rentals and BRRR.

I agree with Collin.At the very least, you need 2nd home, "vacation rental" insurance.

Maybe find a vacation rental that can have personal value for me and my family as well.But more so the attraction to selling would be to pay off higher interest debt (and thereby replace some of that warehouse income).

Glad you made your way here.. are you eyeing long-term rentals or short-term flips?

I wonder if you could look on Zillow or Redfin for apartment rentals that have been unfilled for say more than 100 days.

The Tenant Class greatly impacts rental income stability and property maintenance/damage by tenants.Both Property Classand Tenant Class affect what type of contractors, handymen and property management companies will work on a property.If you buy & renovate a property in Class D area to Class A standards, what Tenant Class will rent it?

Don't be afraid to negotiate, particularly if you have a lot of rentals.4.

I believe the place I am looking at would be a great rental investment but I am not sure if the numbers are there or rather, I am not believing the numbers.

If you want more insights in the STR Market make sure to get our newsletter to stay up to date: https://www.biggerpockets.com/podcasts/short-term-rental None of this matters.