Due to being a complete novice on the topic; I have spent the last few months reading books, attending webinars, and countless hours of driving while listening to podcast.

Completely updated both sides including, new furnaces, electrical plumbing, kitchens and baths.

Sure, it could transform an area and due to cost push low-income people out but I don't think that is very likely.There has been a lot of steam on this, it can work well in certain situations (been sitting on heavily appreciated stocks and want to diversify into RE) but these are primarily low-income areas and the holding periods are long. 

If it's more than $30,000, she will need to complete a simple tax form, but she will not owe taxes.Also, does your wife by chance have a single sister?

Most people do not complete their contract, which isn't always bad. 

I live in Minnesota, and garages play a huge factor in property values (many buyers completely rule out homes without them).

We are looking for a CPA and have 4 rentals - 2 active and 2 in the pipe and try to keep one flip running all the time (4 completed so far).  

Perhaps higher-paid employees would like to buy rentals and rent primarily to other families in their company.I have a staff list with many work phone numbers and work e-mails for both companies, so I can cold call and e-mail individuals directly.

Before you write that down I suggest you start with completing 1.

I will be taking on this endeavor completely solo as well.Knowing all this and based on an estimate of what I would make if I sold now makes it even more difficult as to what path to take.