Could you hold a 2, 3 or 4-plex in an LLC, live in one and still sell the entire building as a personal property sale after 24 months (no cap gains tax)?

You are likely going to pay around 12-14% of your gross rental sales in taxes.

I also agree with the other post on comparing actual MLS sales that have ADUs close to your area vs the cost of the addition.

How much gross leasable area, how many offices, current vacancy rate, age of building, any proximity to hospital or surgical center, what type of loan product for first lien, variable rate/fixed rate, the terms etc ie SOFR + what spread etc, current NOI, cost per square foot, replacement cost per sq ft, and any and all details you can share, I assume HENRY Capital compensation will be similar to your Fund 1, with 8% preferred and 80/20 split? 

I don't see it as selling the home because I would own the lien on the property, albeit I wont benefit from the sale perse.

Smith, Grantor, hereby sales and warrants unto Tom, LLC, a Limited Liability Company created and existing under and by virtue of the laws of Washington, whose principal place of business is 123 Smith Street, and Mike LLC a Limited liability Company created and existing under and by virtue of the laws of the State of Washington, whose principal address is 456 Jones Street, Seattle Washington 12345, Grabtees, as Tenants in Common.

If its affixed to the land I have a product for you.

Quote from @Varun Hegde: According to public records, the property was boarded up in '21 before sale in '23 for $160k.After the transfer, looks like somebody from the city came by and noticed the property was falling apart.

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