A friend of mine invested in one last year—apartments upstairs, a small coffee shop downstairs - and the combination of income streams made it a steady performer.Scaling with a 1031 Exchange:While not applicable unless you sell a property, planning for a 1031 exchange could help you scale quickly while avoiding capital gains taxes.

How do you gain more confidence as an LP? 

If you’re selling and you’re going to buy another rental no matter what, if you probably do a 1031 unless you have almost no capital gain or depreciation capture.

STRs in Non-Traditional MarketsShort-term rentals in areas near universities or event venues are gaining popularity.

I have absolutely nothing to gain here whatsoever so I'll bow out of the conversation.

Start with one property to gain confidence before scaling.

Although the study may increase the gain, the gain may be taxed at a much lower rate making it a beneficial investment.If a property is purchased with the intention to flip or own for a short period of time (less than 3 years), a cost segregation study may not be significant.SHOULD I GET A COST SEGREGATION STUDY BEFORE OR AFTER REHABBING MY PROPERTY?

I’m eager to gain hands-on experience and learn from an experienced professional.

A 1031 exchange would allow you to move into better properties in different locations while indefinitely deferring all tax on gain and depreciation recapture.

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.