Talk to an accountant prior to doing the cost segregation study.You want to discuss whether it will be beneficial or not.In general real estate is considered passive which means that it can't be used to offset other forms of income such as wages, interest, dividends, capital gains, etc.However, there are some exceptions where the real estate loss can offset these types of income.best of luck.

Start small with a single property to learn the process and scale as you gain experience.This post does not create a CPA-Client relationship.

Very large out-of-pocket medical expenses are also part of this game.Balance gains and losses on your investments.

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. 

Upon sale, gains are taxed as long-term capital gains, calculated as the sale proceeds minus your adjusted basis (initial investment reduced by any return of capital).

Quote from @Femi Alakija: As a newbie, I plan to gain a deep understanding of real estate fundamentals, including financing, property evaluation, and market trends. 

But starting with single-family can be a great way to gain experience and confidence before tackling larger deals.If you were someone I knew personally, I would probably suggest multifamily, but it's not for everyone.

Headquartering business in CA has tarnished, and too is being assaulted like never before, and gaining traction.

My best advice would be to begin networking as much as possible and find a mentor.You've already taken the first step which is gaining knowledge.

It takes longer to realize, but the gain is worth so much more than a couple hundred dollars of cash flow a month.