If SF can be turned around, I think it could make a lot of sense if you understand the intricacies and can put up with the tenant/landlord law for the long term.  

Just run the numbers and make sure things make sense.

Is my out of box thinking not make sense and be a waste of everyone's time?

From there once a deal makes sense, pull the trigger, a lot of folks get stuck in analysis paralysis and I’m not saying don’t do your due diligence or be smart about it, but acting quickly and with intention will benefit you greatly in the long run.

If you ask for a CMA from a local PM, you will be able to make sure the numbers make sense before you buy!

If there is no difference between Carrot and WordPress when it comes to SEO and ranking on GOOGLE then it might make sense to go with WordPress for a long-term play. 

It makes sense for a PM to be Additional Insured on a landlord policy because they can't get insurance coverage on a property they don't own. 

Congratulations on the duplex -My investor clients have acquired several multi-family investment properties locally in the market I operate in Northwest Indiana - Figure out your personal investment objective for the next 4 years and align yourself with the next property that make sense in this current market environment-

Unless you have some ridiculous deal and need funds to close it now, then it makes sense to refinance in 3.5 months.

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.