If let it get outdated and go into disrepair, well, that will dictate the clientele we can attract right. 

Here’s my two cents:Paying off the condo might make sense if your main goal is to reduce risk and enjoy the peace of mind that comes with no mortgage.

To 1031 it doesnt make a lot of sense IMO since $100k of equity going into a new property with 7-8% interest rates will force us to look into markets outside of Oregon, require a Property Mgr at 7-10% and we're almost back at square one unless its a MF with great cashflow.The main considerations for liquidating the brokerage account are: capital gains + OR state income taxes will be brutal, I like the idea of tax advantaged real estate gains AND growing real wealth and assets, not paper wealth.

It all cash flows like a gold mine until the roof needs to be replaced, the main line goes, or you get your first turnover bill and need to upgrade a kitchen. 

My main question is whether it makes more sense to go the seller financing route and pay off the principal in 8–10 years or stick with a standard 30-year loan.My thinking is that the tax deductions from a mortgage wouldn’t outweigh the potential equity I could gain over those 8–10 years.

Lenders stopped allowing rent by the room due to modifications done to the property resulting in functional obsolescence and significant cost to cure in the event there was a default and they needed to foreclose on the home and resell it, given that the main buyer pool for single-family homes are primary occupants. 

Can you share what main use case that you propose to utilize our solutions would be?

A longer timeline will make paying the extra 2% now more attractive.

Is that the main goal or something else?

These areas are super attractive for investors.It's not hard to see why.