It seams like an area that is starting to improve and is pretty close to the Grosse Pointe areas which are pretty nice and pricey here.The asking price on the property is $46,900. 

Is this a new improved 1031 exchange?

If I buy a property in need of work or improvements my after repair/improvement revenues are fairly predictable because they are based on what that market is generating today for a similar property.

The truth is that you have to play by all of their rules in order to get a decent search ranking.I wonder if Airbnb is the same?

If I have found a "good deal/discount property" for 285K-300K that needs 15-20K of improvements.  

Refinancing and paying off that FHA loan as well as pulling all my cash back out from the rehab and hopefully more, does this work this way or is there some rules or regulations on this specific kind of thing that would prevent me from doing this?

Whereas, if you turn that illegal garage unit into an ADU, and  youre using the existing footprint (not adding on), there is no new hookup fees.The rules have been changing a lot lately.

If you're getting good deals on the investment properties, that will actually improve your DTI, assuming an investor friendly local lender that isn't riddled with rental income overlays such as "rent must appear on two years of tax returns for us to 'count' it."

What improvements you personally added with $500 on this awesome home ?

If you decide to continue with the FED, let's assume the judge rules in your favor... that ruling is likely because the tenant did not show up for court.