Find out if you can tear it down, and if you can re-use the foundation, what is the property zoned for and what else could be built there, if it will need any special type of soil samples or other things of that nature that could get expensive, etc etc.

More pressing, is my worry that I don't have a stringent enough vetting process in place and sometimes I let my good nature get in the way of making educated decisions.

I would naturally like to make passive income on cash flow opportunities following the BRRRR method but rent seems difficult for the price of the housing at the moment.

When the two naturally come together I will know the right time :)

If it could be more like a small apartment complex or something of that nature but then still have the amenities of an extended stay. 

So, rock on - but don't hire that family member to keep the books!

You'd naturally want to push away from the downtown square.If you look south, you'll see Youngstown. 

They are by that nature, very restrictive! 

We lucked out and contacted a rock star Realtor who found us the right investment properties in the right areas at the right prices and was worth her commission (and then some!)

We don't live in a cash flow market necessarily, but if you're west of the 5 in North County coastal, you'll be good in terms of natural appreciation.