With the fires in CA, you can expect materials and contractors to become even more expensive. 

From there you can start to identify what you are looking for.Where do you land on the follow spectrums:Cash flow and AppreciationLong term or Short term needs (waiting for growth vs get out of my W2 now)Long term rentals, Mid term rentals, Short term rentalsBuying close to home or coast to coastSelf manage or hire a PMIf you can narrow in on those, you essentially have your buy box. 

We have renters there now and they cover the mortgage with a bit of cash flow ($100/month), but the property is going to need some more major updates (windows, roof, HVAC, siding) within the next 5 years as they are starting to be at the end of their useful lives.We would like to pay off our primary residence as quickly as possible to “free us” from mortgage payments on our primary residence.My questions are below:1.

Kid in college and one starting to drive   blah blah blah.I'm sure there are numerous places to cut money for sure. 

I've been going about as long as you have and things are starting to come together and happen for me here in Sacramento.

You can't just take what you paid and start charging interest on that figure, because part of what you paid was already accrued interest.

Excellent start. 

Hey George, congratulations on starting your real estate journey! 

I'd start by giving all residents the required notice (usually 24 hours) and go inspect the units as quickly as you can. 

@Juliann Morala if you're going to rent it out, start with a PMC!