Retirees looking for tax advantaged strategies to buy retirement home in Maui!

[Marc Estepa]

It’s been awhile Bigger Pockets Fam! Posting for a friend. My friends’ parents are in their 70s and retired in California. As they have gotten older, they have been seeking warmer climates and want to retire in Maui. They currently own two properties, their primary residence in the Bay Area where they owe approximately $300k and a rental property in San Diego where they also owe approximately $300k, but have about $400k equity.

Their goal is to snowbird 6 months out of the year in Maui, Hawaii, maintain their primary residence in the Bay Area and figure out the most tax advantaged strategy to sell their rental property and use it to buy their 2nd home in Maui. They are also looking to house hack a portion of the Hawaii home to help offset the costs of that 2nd mortgage.

They have pensions that pay for their day to day living expenses, but are just reaching the age where they must take their RMDs from their other investment accounts (which they don’t need at the moment). As a result, they are trying to find every tax advantaged strategy to do all of this without getting crushed on taxes. Good problem to have!

Anyway, they had reached out to me for my take on it and I think a 1031 exchange would be the best way to go about it, but I’m no expert. I suggested they talk to their CPA to ask specific tax questions to better understand the tax implications with everything else they have going on with their finances, and this has led them down the rabbit hole of reading tax codes and the such. That’s just painful, so it quickly discourages them from pursuing their retirement goals and just settling.

I think they have the pieces in place, but are surrounded by naysayers who don’t understand the real estate investing world enough to help them pursue their dreams, or others who simply discourage them. I told them that their first step would be to surround themselves with others trying to pursue similar goals. So, I naturally pushed Bigger Pockets.

I’m not the real estate investor expert, but I think they have all the pieces in place to do this - but wanted to hear from the community their thoughts. Am I advising right or are there other strategies you can think of to help push them in the right direction, maximize their income and avoid taxes as much as possible?