Most people do not know this is a legitimate way to fund your real estate deals and do it in a tax advantaged way.

If Costa Rica gives more capital gains like you suggest (which I doubt given how pricey it already is), he's going to get them with his own property and he'll ba able to take advantage of it without needing anybody's consent.I think the question is whether you can lure a lifestyle buyer into seeing it as a better opportunity than if he'd own his own property. 

This opportunity doesn’t occur frequently but it takes these attributes to take advantage when they do.3 - Blind luck - do enough deals, the unique opportunity tends to present itself.  

I would look into assets that are non-correlated to the stock market or real estate, as well as tax advantaged assets to help shelter your income. 

A post on the official Norada Capital Management website from 2022 (attached screenshots in addendum), boldly states the following:“Norada Capital Management offers investors opportunities to invest in Promissory Notes with fixed rates of return ranging from 12% up to 17.5% per year,” ( Link ).In explaining the use of proceeds from the promissory notes—specifically the entities Norada Capital Management, a private equity firm, supposedly lends to in order to generate these high annual rates, the company states that:“Three of those five categories that our company invests in as a private equity firm include e-commerce-based businesses very lucrative area, especially if you’re in the right area of e-commerce.

With experience in construction and sales, you'll definitely be able to use those skills to your advantage when doing value-add deals.The better the deal is, the easier it will be to do the BRRRR method and you can find some of the best deals off-market, so it's important to build a solid network and create deal flow so you can see as many opportunities as possible. 

If you decide to sell and find an investment property with a greater cash flow potential.A 1031 exchange would allow you to indefinitely all of the tax and use it to your advantage to reinvest into larger nicer property/properties.

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.

On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

I don't think anyone goes to CA to invest, but a lot of residents invest local to keep the home-field advantage which is a valid point..