@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.

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.

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.

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

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

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

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

Do they think this will just happen on auto pilot and they can attain the same as me?

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.