Ideally, we’d like to sell both of the rentals, and use the cash to place a down payment on a larger multi family home investment property, maybe valued somewhere around 400-600k.

If you’ve ever though of retiring outside of California that could be the ideal place to buy a “nicer” property that someday may work better as a primary than a rental.

That's not ideal but if you can make the numbers work, then go for it.

Buy to let, and of course BRRRR would be ideal if possible. 

It is ideal to get as many stays as possible before yearend.

I deal with all the paperwork and the negative side like chasing unpaid rent and such but my property manager is amazing and deals with the day to day inspections, fixes, tours and most the communication.

I deal with a lot of problem tenant solutions in my state. 

Signalized access, ideally with turn lane and signal, but at least right/left in, right/left out.  

Ideally, I would like the old contractor to finish/fix his work that they did but Im not sure if it's worth the hassle given our time constraints.

@Connor ChatlosDenver and Chicago's high property values make multifamily properties ideal for house hacking.