Buildium, Appfolio, or Yardi are some ones to pick from. 

I do appreciate the no hassle and quick credit for spam leads or duplicates when I make the request, although it would be great if the system picked them up in advance.

Very unusual and foolish for a lender to allow a borrow to pick the appraisor. 

Some areas that are on the path of appreciation and aren't yet completely picked over include Little Village, Hermosa, Belmont Cragin, Mckinley Park, etc.I am a local investor as well as an agent so if you need any help please don't hesitate to reach out

@Sharad BagriI would pick up the phone and call an attorney.

The issue for you is you (or your wife) now may have two insurance carriers fighting over who will pick up coverage (assuming your intermediary LLC has appropriate insurance) or if it does not, your property insurance carrier may try to get out of coverage because of your slick deception tactic of using an alter ego which is the last thing you would want.Just  yesterday another BP forum poster wanted advice on a similar strategy when leasing a rental cottage on the same lot as their residence.

We're picking up extra work, multiple side-hustles and cutting living expenses... what am I missing here?! 

Picking a house with major, costly structural issues or in a location with poor rental demand can hurt both the rental and refinance phases.

Try some Ohio REI meetups or social groups—you’ll pick up a lot.

Pick an option then execute.