Sometimes they’ve got resources or connections that could help speed things up.What’s your biggest concern going into the hearing?

Leave it in there.

If you are concerned it will be too hard to find a renter, lower the price and rent it for three months, then place a new tenant at the higher rate after winter.

There are significant details that I'm choosing to leave out regarding rent payments and balance left for the owner as you terminated the lease early. 

Both properties won't leave you with cash flow, since you will need to use that for turnovers etc.

If you have a concern, are you able to talk to them?

I have a few concerns that I wanted to get people's thoughts on. 1 - Selling a quadraplex 10-20 years down the road seems like it may be challenging as the market for that type of asset is small.

One of my original mentors was PRO lease option on the purchase side, however I never felt  peace about it.I was always concerned what if something happened to the original seller and they did not cooperate when it came time to exercise the option. 

Putting a long term tenant in a property here that you are BRRRRing won't cash flow unless you plan on leaving a good amount in the deal to do so, but that defeats the purpose of the BRRRR. 

You can certainly leave money in your BRRRR - it doesn't have to be the "perfect" BRRRR that so often is talked about where you pull all of your investment out and then some and therefore have infinite returns.