@Michele RichardChicago neighborhoods and suburbs are ideal for rental properties and Building Reconstruction Redevelopment (BRRRRR) due to proximity to major development projects, affordable multi-family units, and strong rental demand.

You ideally don't want you purchase price + rehab budget to exceed 60-65% of the ARV to properly BRRRR, as most of the time you'll only be able to refinance at 75% of the ARV.

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.

But for vacant properties, I think a 'show and go' policy would be ideal: the buyer’s agent can confirm directly with the listing agent, and then they’re free to view the property without delay.

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

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.

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 a lot of problem tenant solutions in my state. 

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.