Is it better to sell, pay off mortgage and capital gains and take the cash to invest in another property or is it better to refi/ETO and take the cash to invest in another property?

Be mindful of short-term capital gains tax, as profits from flips held for less than a year are taxed as ordinary income, and frequent flipping may result in self-employment taxes.While profits from flips do not qualify for 1031 exchanges (since flips are considered inventory, not investment properties), you can minimize your tax burden by deducting allowable expenses like renovation costs, loan interest, and holding expenses.If you're considering diversifying into rentals, explore opportunities to benefit from long-term tax advantages such as depreciation and lower long-term capital gains rates.

Either way, I hope this provided you with some insight and I wish you the best!

I would be happy to forward you the contacts of these folks so you can reach out, as well as a referral for a short term rental consultant who may have some insight.

Hope some of this insight could help with your decision if you decide to take the leap! 

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

Recently, our real estate agent did a market analysis and estimates we can sell for between $575K-$585K, resulting in a net gain after all of our fees of about $100K.

I thank you guys for those insights.

Thanks for your insightful response!

With everything paid off, they’re looking to slow down but are hesitant to sell due to capital gains considerations.Purchase Price: $1,750,000.00Downpayment: $400,000.00 - Will do a 1031 - Selling two of my SF properties for the downpayment (bought for 120k + 146k back in 2017 & 2015).