Hey @Jimmy Jarjour
It sounds like you are crushing the education game. Their books and podcasts are loaded with great material.
House hacking can be beneficial for soooo many reasons as many in here would chime in with.
If you're already looking to connect with a rockstar agent and loan officer/lender, then you're going to be on the right track. Networking will give you some people to lean on for questions and to fill in the other blanks i.e. contractors, insurance agents, inspectors, property management, etc.
I'd definitely agree with @Rick Albert. I am not necessarily scared of the age, but more so weary of the cap ex age and building materials. For example, brick homes can last hundreds of years if taken care of compared to some new stick built development homes. A 1920s home with new plumbing, updated electric, and a new furnace might be in a better position than something from the 1990s. That 1990-2000s home might be reaching the last leg of all it's cap ex items.
Lastly, in HCOL cities, house hacking may give you the opportunity to live in an area to enhance your quality of life. For example, maybe a house hack where you are offsetting your housing expense allows you to live in the heart of three key quality of life factors (Where you work, where you leisure, and where you shop). This is compared to if you bought a standard residence 1-2 hours from where you do those three things. I know for many in the Bay Area this has become pretty standard unfortunately.
Good luck with your HH endeavors. I'm happy to connect to provide any helpful insight.
-Ant