Feel free to PM me and I'll get you specific referrals. 

I believe that if you are well versed on a specific market, or have someone who is knowledgeable in that market, you can do a successful BRRRR in another market as the local will likely have everything you need to get set up! 

My offer did include an inspection contingency which I would not be willing to remove, but they didnt seem to have an issue with that specifically. 

Finance your first duplex or triplex through FHA Loan, Conventional Loan, Owner-Occupied Financing, and Portland-specific programs.

The best strategies will be tailored to your specific situation. 

Any specific workshops, courses/masterminds, or maybe finding someone that's willing to let me shadow them? 

Without more details about your specific goals and experience, it's tough to give real tailored advice.

I would not invest in real estate with a retirement account.Its too much of a headache and likely not that much better as an investment alternative within a retirement account1) Real Estate provides tax benefits for individuals who own them.

Alternatively if you feel confident in the higher value, I would ask if the lender is open to doing an independent appraisal ordered by an AMC instead of a desktop one. 

As an alternative, would a cash-out refinance, a home equity loan, or a HELOC make sense for you?