It may work out, but I feel like more often than not your buyer would go over budget, and your business would suffer from selling bad leads.

You need to work out the closing cost, selling fee, escrow cost of your current home see how much of that $20K equity is left.

I should use this to test my discipline, it will work out way better in the long run.

How did this work out for you?

You have to understand the specifics of the situation and OH law to figure which is likely to work out best for you. 

Yes, no, pretty much, depends on what you and the GC work out.

I have never done house hacking before since i married most of my life, so unsure how well this would work out, currently im single so no more wife issues on this one. 

To me we are just entering into what has always been a fairly normal market in good times.. and for me its always been value add will always be... if folks don't want to do that or have no capacity then its the old buy and hold.. and one can do that but just need to do it for decades to make it all work out given the ups and downs.. and no better time to start then now.. especially at these interest rates.

Easier to shoot for in active investing (e.g. flipping) though that comes with risk and is more intensive. 

(TY professor Chichernea for one of the most intensely challenging Corporate Finance classes ever!)