Based on the knowledge and experience you have, would you consider this strategy if you had to go back at my age?

@Jason Brown - I'm a CT based investor, flipper, and property management company owner.  

In the end, buyers would overpay for the actual property based on earnings.

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. 

I contacted ALE solutions on Friday through their housing request form and just resubmitted with a longer term minimum based on what you stated here.

Does anyone here have any idea (based on data), if the home prices will be going up or down in 2025?

They will base their DSCR calculation on the market rent 1007.

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.

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

@Jaycee Greene I am looking to buy a primary residence while I am based there, then turn it into a rental once I PCS again two years later.