For someone looking for diversification or steady long-term growth without getting too hands-on, your suggestion of buying and upgrading a rental property in a familiar and appreciating area makes a lot of sense.

Sometimes I actually walk away from the deal - Not All Creative Financing Deals Make Sense. 

This is a hard pill to swallow, but one that makes sense due to the higher risk of this being my "first deal". 

Dennis' dad and I actually tripped over something similar back in Chandler.. we learned to tap into city planning websites and even call the permit offices directly to get a real sense of their backlogs.

I'd say just start your search with all 2-4 unit properties, and when you find one where the numbers make sense and it checks your other boxes (somewhere you actually want to live and house hack), then it probably makes sense. 

This doesn't make much sense.

Quote from @Andrew Rodriguez: @Theresa Harris: You make sense.

This setup alone feels like a solid foundation for financial freedom.Here’s my dilemma:While I understand that my mortgage interest rate is very low (2.8%) and there are tax benefits to carrying the debt, I’m wondering if it might make more sense to aggressively pay off the loan.

I tend to agree, in this uncertain investing environment it makes sense, it just feels weird to have that much cash not working for me. 

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense.