I don't exactly follow what you mean by "where we are in the cycle," but assuming you mean that RE is at or near it's peak in value, that would not influence my decision, especially if I could pay it off within a couple years with my W2 income.

I also think it's our duty as consumers to review people we do business with- whether the experience was good or bad.

I keep doing the numbers and feel like the numbers are showing bad deals, but it doesn't make sense to me how they can be. 

Go to www.narpm.org and search their directory.If you make a mistake and hire a bad Property Manager, it can ruin you for life.

I would not keep throwing good money after bad.  

@Max Tanenbaum - Not a bad idea haha.

Worst case scenario you lose your earnest money and create a bad rep for yourself.

No court entries on the case file on Judiciary Case Search since September.The property is not in particularly bad condition. 

It is good to understand and decide where on the spectrum you want to operate, but it won't influence your analysis very much.https://www.biggerpockets.com/blogs/4445/36354-041...

Pay off bad debt before REI if possible