Septic is risky but do-able. 

If I were to expand upon the main house and make it 1400 sq ft, which is definitely doable, would I then be able to turn around and get that section closed off and convert it into a 500 sq ft or less JADU?

It does take time to build clientle and it does take up a lot of time but totally do-able!

Never hit the snooze button.

You’ll see if you dig that there is a constant need for good PMs...and it’s a very challenging, intensive business...but doable. 

The rates are higher, so harder to make it a deal, but still doable and is essentially a step in the method once you've reached that point.

I do know a few that still continue to do AirBNB to this day in Vegas - risky but certainly still doable.

All title companies know what a double close is.....the problem is if you’re trying to use the end buyers money to also close the A to B transaction.....here, that is not doable. 

@Bradley Fisher sounds to me like you're set up and I wouldn't worry too much about timing, just buy right (which includes trying to buy at a discount which should be more doable in smaller/rural areas of Ohio).

If you are willing to look at some of the outlying towns near Portland house hacking to live for free is very do-able.