@Leslie L Meneus, while the forums can be pretty good, in-person networking and sharing ideas is much more valuable.  

If you're more of a 'personal referral' person than a 'do research online' person, and this is local to you in Manhattan, KS, hit up one or two of the trades people in the "little apple all stars" BNI group.

To Sum it up, its a good idea if you can exceed the cost of capital (higher rate than your cost of debt) with what you earn on your heloc/debt you pull out and invest.The question is how much gains above is enough to substantiate the risk of your variable interest rate, well thats up to your personal investing criteria.

This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.

Focus on the numbers and the goals, not personal feelings.

These homes are in my personal name right now.  

I doubt he'll be able to quality for a loan (VA) with just his income. 

Personally see these laws sweeping the nation.. 

@Avery Oblepias in general, paying for something you can learn online, is really paying for convenience and discipline.It's no different than paying for a personal trainer at a gym.Regarding S8, it's a pretty basic program that $5k seems a bit excessive for.Maybe, $1500?

Generally there are multiple units for each "zone" if you will when I've seen them installed.Regarding your problem at hand, I personally would simply adjust your plan to move and make your initial plan to get the current issues resolved, while costly now, in the long run holding onto the unit will likely pay off.