Howdy @John VoychickTo make the BRRRR strategy consistently work over and over you will need to stay within your investing criteria.  

I don't know what it is, but every unit that I put stainless in rents in minimal time, while white appliances seem to stay on the market a while.  

To be most profitable, know that you shouldn't stay at your property during those times.The easiest route for you would to buy a Condo-Hotel.

The other 2, their house burned down and their insurance company is paying for them to stay in a STR for 3 months. 

I don't care how close I am to the person staying with me, good boundaries make good housemates and I'm the one who is at risk if bad things happen, not the ones paying me.

But I love living in the city where all my friends are so I was then restricted from there to my income, but I also wanted to stay in the area.

Im looking for one where the landlord and Prop Mgmt company goals are aligned (finding good tenants who stay long) and not trying to uncharge on unnecessary  fees when possible.

Just between the increased Vacancy amount and insurance I believe it will wipe out your Cash Flow projection.You will find it in your best interest to stay conservative with your numbers.  

My wife stays home with our 2 kids and is unable to work.

We may have to move out of SF but would like to avoid that if we can.I've considered the following:1) Stay in our current 2bed/2bath as long as possible (likely 5 years max) or until the market softens2) Sell now, rent in SF, avoid taxes and free up gains for other investments and wait for a market to soften in SF or move out of the city in a couple of years if it doesn't.3) We'd love to keep current home as rental after buying new home.