I put an offer in on the rental I currently occupy, but came in under where my landlord (and 1 partner in this property) were looking at to even entertain giving up a cash flowing property. - He bought this 4br/2ba for 285k put 20k +/- in and I rent for 2700.

You want a short term rental policy like @Garrett Brown listed.Regarding the 1m liability, we have 2m and a 5m umbrella.Now this is going to depend on where your STR is.

I have wholesaled properties like this in the past, but I'd like to keep this one for myself if possible. 

I have this plan where I first start out with a duplex , Rent 1 live in one for a year move back in with my parents and then leverage off that duplex to get another property right away.

When I decided to dump the last PM, I went on my community FB page and asked for recommendations.

Does the property actually need this repair?

You can click on the magnifying glass in the upper corner and research previous times this has  been asked and answered.

This implies that rather than pay the loan early, you are likely to do better putting that money in S&P or you can do far better using it to make a smart RE investment.- current f/f is around 6%.

What benefit does this provide them?

I would be very happy to schedule a Zoom meeting and compensate you for your time spent mentoring me on this subject.Thanks,Kevin