Since you said you don’t really need the cashflow because you are sitting on huge reserves do the math based on income instead of cashflow.

In that scenario Section 8 tenants are the least risky tenant base. 

Based on your situation, you will likely need to recapture the depreciation when you convert the property from a rental (STR) to your primary residence in 2025. 

Some agents will not take less than 3% no matter what, others will adjust based on the deal. 

Unfortunately, from a STR prospective it seems like there is less opportunity based on supply/demand and current home prices in the immediate area.

The guest house has STR rental history but the other two units would need to be based on projections. 

DM me so I don't lose you, we are not based there (CO-based until probably 2033)

In Oregon for instance unless your doing a PUD open space cannot be required and you MUST create lots to specified zoning density.. in other words if your zoned 5k sq ft lots U cant ask for 7500 sq ft lots you must be within 10% of the base zoning.

So it would be best for him to first understand how this would impact his taxes and estate planning then structure the sale based on that.

Yes, as S-Corp owners deferring salary into a Solo 401(k), you must still pay FICA taxes (Social Security & Medicare) on the deferred income since FICA is based on W-2 wages, not taxable income.