Is there a way to reduce that huge capital gain hit?

A good plan will show how to structure things like your wife’s business, potential rentals, and depreciation so everything works together to reduce your overall tax burden while transitioning away from W-2 income.

Quote from @Santos Lopez: I heard that there's a way to deduct short term rental losses against earned income (e.g.

I earn 4% for a 6 month term and every 30 days one matures and I roll it over (usually adding additional reserves). 

Reduce hold time by lighter rehab, getting deals that are smaller in sf, do not need landscape/exterior work (I.e. condos)4.

I have not done rent by room in many years but my son is currently doing it to live at reduced housing costs.  

These two elements often get overlooked in the excitement of deal-making, but they play a critical role in the long-term success and sustainability of your investment journey.A well-thought-out tax strategy helps ensure you're maximizing all available deductions, utilizing the most favorable tax structures, and ultimately keeping more of your hard-earned income.

There are strategies that you could do to try to get future paper losses reducing your active income, but those require you to change your income-earning activities.

I am the founder of a transitional housing programs that will be offering services to returning citizens and residence that are at risk of homelessness. I am hoping to lease a 4 to 3 bedroom townhome and I am looking ...

Lastly, this rate reduction would increase guests disposable income as credit card interest rates would reduce also.