Thus, my main goal joining this forum is to try to gain confidence in the decision to get into real estate investment and better understand the risks that I may not be considering due to my lack of experience in the field.

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.

The problem is mainly a concern for people with a net worth or reasonable income. 

Mainly marketing themselves.

Their main sales pitch is that they will teach you how to make more money by charging your investors double the industry average acquisition fee.  

As far as I know, your assumptions about the tax implications are correct for non residents, it was one of the main factors that stopped the idea of investing in Spain for me.

STR in Boston (and metro) are mainly for owner occupied residents only which means you can rent your bedroom or an adjacent unit.

To you there was little change, you just keep paying your note but now own 123 Main St instead of 345 Side Way, and you have your equity as cash in your pocket from sale 1. 

OKC has alot of opportunity mainly because of its low level of enforcement of housing codes, strong landlord laws and conservative judges in eviction court.

Yes, we meet the 1st Thursday each month for our main evening meeting and we meet the 2nd Saturday each month at 8am for Dealmakers Breakfast Club.