Leasing at $3k/month covers your current mortgage comfortably, so refinancing could relieve the pressure of the balloon payment.

They are subject to liability if someone sues, and their license is subject to discipline or loss of license if you violate rules/laws and get caught.

Keeping this as a rental would not cover the mortgage (we'd have to pay ~1500 a month including utilities) and we can afford the extra payment, but is it worth it when looking at appreciation?

So make sure you can cover both loans for awhile. 

One note is that if the property was helping cover my costs of living while I house hacked it I wouldn’t worry about negative cash flow while I resided there.

You have to do the work on the front end and vet out who you are listening to about the subject you want to learn about.

One was making an extra $600/month while covering all of his household expenses with just 3 PadMates. 

Quote from @Bruce Woodruff: So that's 7 months......now investors will have to add a bit into their flip budget to cover the extra 3 months (or so) holding costs... will make overall costs go up though... 

Could I send you a DM on the subject?

I think you'll also find that even if he isn't liable for the debt, his interest in the property is subject to the lien of the mortgage.