We plan on being able to pull out 55-60k on the refi (mortgage under my name) , and the property rents for 1,395/month.

Ideally i would then like to use Rental Income from AirBnB to pay off source of funding for rehab on primary residence and being able to pull out profit from equity gained to use on another real estate investment.

Lastly, the pay structure with JB was so completely confusing he ended up pulling out.

It may also be why she rented from you vs someone who does credit checks.At this point, I think your best strategy is continued gentle pressing.   

We normally give ourselves 2 full months of keeping both in action to work out bugs with our vendors before pulling the plug and even then we find things we missed (some random vendor will auto draft out of our old account)In fact, even asking this question is starting to make me dread the thought of switching.That said -- it's time.  

The only true way is to pull up comparable sales and analyze the comps and condition of the property. 

It’s finding the right educated/experienced contractor to pull it all together is the trick. 

I'll pull the trigger on that!

My initial propose for obtaining a license was to pull comps myself and make my own offers.

In any case, when I searched for the owner’s name, I came up with the 2 mortgages but nothing else.Also, I saw that the same property was put up for auction last year and then removed – is it likely that the owner paid off what was owed then and fell behind again or do banks just arbitrarily pull properties off the auction block?