Commercial and multi-family real estate are great choices in Houston.Good luck!

I've established a very stable  I've determined that local properties should be my first choice and by local I mean within 1.5 hours of my primary residence.

Hi there,Given the complexity of your situation—owning a rental property in Florida while residing in Illinois, house hacking with your daughter, and planning to claim tax breaks—it might be a good idea to consult with a Certified Public Accountant (CPA) or an Enrolled Agent (EA) who specializes in real estate taxation.While your current tax professional at HR Block has experience with multiple properties, a specialist can offer more in-depth knowledge on multi-state tax issues, rental income reporting, depreciation, and maximizing deductions specific to real estate investments.

So, be prepared to learn a LOT or to hire or partner with people who have the knowledge and experience in these other areas.

You could have made the choice to capitalize them but likely not.

Bite the bullet and replace it Cheap probably was not the best choice of words for some people. 

Check the in person events and meetups in your local area, our online community is full of knowledge and folks willing to share and still nothing replaces the opportunity to interact IRL, you never know who you will meet and where that can take you on your REI journey. 

Is it just based off knowledge from experience/visiting with boots on the ground/from speaking with other investors/realtors?

There is a plethora of knowledge here and some great resources. 

Lots of good knowledgeable folks on here, and good local PDX/VAN people as well.