Many people aren't uncomfortable enough in their current life to make a move. 

@Manoucheka Guillaume we routinely sell properties that are legal non conforming here in the Chicago suburbs.

@Tyler DeVerse there are a lot of us that routinely direct mail the small multifamily properties here in town.

Find people who work the territory you want to play in.A broker who routinely sells 200 to 300 unit properties is probably not the right broker if you are looking 20 to 50 unit deals.

If it says you should leverage your RE, then use it to buy more, if it says you should de-leverage your RE, then put it there.Having said all that, it's clear you are uncomfortable with the risk you have, so the my advice without knowing anything about your IPS (very dangerous, for you) is to pay off debt.

But then he should stress the important items (if any) like - "this house is in overall good shape, just some routine issues and they are in the report, please read the report thoroughly.

We've gotten into some pretty unproductive conversation about "how in the past 10 years he hasn't needed a sewer inspection" and how I "am routinely scoping up properties for BRRRR in Kansas City, and how a sewer scope was included for each property and actually saved me from bad deals" ... 

That being said, I’m still willing to take that risk with the same mind set as all other risks I’ve taken… “it’s uncomfortable but there’s no plan A, fail forward and conquer it”.

What are routine (monthly, quarterly, yearly) maintenance stuff I should do to make sure my rental is in good working order.

It was either this or go into health and wellness and become a personal trainer/coach/nutritionist as that fits my lifestyle and routine.