There are other options such as harvesting capital losses on other financial instruments, but the stock market has been pretty good lately, so that may not be an option.

There's a high chance that you are feeling FOMO from the returns in public markets, sell your houses for a loss, pile into stocks, and then see mediocre performance while real estate heads back higher again.I see this, and similar actions, play out over and over.Personally, I'd stick with the real estate rather than selling it.

Sorry for the following Contrarian advice, but you're not a 5 year old so:The only reason to buy a personal residence (Home) is because someone is forcing you to.Usually, this person is called your Spouse (which is Latin for someone who forces you to make horrible financial decisions then criticizes you for them endlessly:)perhaps DON'T buy a home, just rent something affordable and invest the 20% or in your case 50% into the stock market (sp500 16.1% yearly return last 15 years, 11% last 50 years, 10% last 125 years)remember, your RENT is your maximum monthly housing expense, but your Mortgage is your minimum or starting monthly housing cost, it always goes up from thereI've, owned 2 personal homes, 100% appreciation in 6years on #1 and in 7 years on #2, (I timed our market perfectly both times), with 20% down and very low mortgage rates, but after honestly calculating all expenses, only made about 5-6% a year "investment wise".

As expected, he recommends Roth conversion and invest in stocks. 

These rates of return surpass what bank-provided bonds and stock dividends offer.

One other point to add is considering donating appreciated stock.

Investors buy shares and earn returns through dividends and potential stock price appreciation.You typically can’t lose more than your initial investment with publicly traded REITs.

This has been my strategy here in NOVA as well - though true multifamily housing stock is hard to come by as you are probably already aware.

I would expect start-up costs such as stocking linens/bedding, upgrading certain furnishing and amenities, and pass-through costs for listing on the OTAs (like VRBO, Airbnb). 

For others, it may be diversify into stocks.