Heck, some people might even pay more for the 'cool factor' of living in a 'small home'....I'd give it a go since you're a veteran of this RE stuff.

My goal is to be filthy rich and set my family up for generations. maybe I should pay the mortgages faster?

I just want to get financable this year - pay off debt, save some $. 

Its all legal and now you only have to maintain a place for 5 groups. 1) you can get a heavy cash deposit down for the ownership. 2) they pay quarterly for expenses that funds the overhead. 3) everone has a share of profit when you or they decide to sell for a higher price.

My big bold move was to rent them at $150 month with tenants paying for heat and electric. 

@Jason Wray Thank you very much for this response ..I’ve never sold one of my rentals before feels like I’m cutting off a leg and paying close to 100k for cap gains is really starting to eat at me 😵‍💫Any chance you would be so kind as to send me a link to something in the ballpark of what you’re suggesting this way I can get an idea of area and what this type of property could look like!

The only time I'd say it's an okay idea is if either: The area you're investing in is expecting so much appreciation that you will easily profit off that (watch out for mortgage interest though...the appreciation needs to be higher than what you pay in that and expenses to make it profitable)You have some specific reason for wanting to do it- family ties, future home, major long-term hold, etc.Maybe I'm forgetting another one, but those two are all I have for now...

I wouldn't be opposed to having a little skin in the game (closing costs, inspections, etc) I would be living there paying market rent and doing the improvements myself.

pays your mortgage while you make Cash-Flow on those properties that you have under your name that pays you a higher ROI every Year.

To be fair, I've encountered situations where the Section 8 rent received was higher than what cash paying tenants were paying.