Those listings really don't tell you much about the trend unless you have a spreadsheet you've been keeping secret.

I’ve lived in my current home (Raleigh) since 2018 and I’m hoping to keep it, but have several questions.

I could refi out to a tradition bank and keep it as a hold. 

Keep in mind you are liening your residence on an investment which is risky. 

I have a 1900 year old up and down quadplex that I keep getting complaints from the downstairs neighbors about the above tenants noise level.

He can't even keep them straight, Might want to find an app to keep his lies and fraud straight.  

This is how the tax/book keeping side works.

Keep in mind this will take a lot of research into the local market but there are plenty of opportunities in Milwaukee.

Of course you can refi, but you wont be able to do a full cash our with rent covering your mortgage so you can keep rolling the funds to next project. 

I am about 9 years in the roomie/tenant house hack (where i basically PM'ed for the LL from the inside); and about 2.5 years in the roomie/LL bucket. one piece i will add, i try my best to not "call shots" and keep things pretty democratic/ open for dialogue discussion between everyone. unless its a safety issue (or a liability issue, like guests can be)... i prefer this to be "our home" instead of "my house".