I go back and forth, but I also think the best teacher is experience, but would like to hear your thoughts.You'll never learn everythign as there are dozens of strategies implemented by Real Estate professionals, but if you're objective is to househack then there's no need to wait.

Buying at this price point also allows for me to make extra principle payments, forcing more equity and a forced savings of sorts.

The objective was to get the home online and block the dates.

I can get better CoC/cash flow there but it also requires more money up front with having to put 25% down on investment properties - I currently have one duplex in Milwaukee. 2) Buy a much more expensive 4 unit (700-750k) with an FHA in Chicago, cash flow around $150-200/door once I move out BUT get far more principle pay down , gross rent and appreciation.

In principle, therefore, our lawyers have recommended C4K deals wherever and whenever possible to avoid court outcomes and timelines. 

If you have no money in it and the tenants are paying down the principle I would keep it.

Looks like you and I have similar investment objectives. 

I’d write the inspection objection asking for a considerable discount (at least $50k, ideally more).

And they're trying to create an objective and measurable way of tracking it.

The favorite thing about this book is that it is packed full of real estate investing principles that one can use in any asset class.