I don’t think the tiny house would get you there.

It's an STR, hotel and house hack all in one 😊

Condo regimes are popular here and I’m thinking maybe converting mine to a condo regime and sell either the back lot or the front lot with house and keep the other.

Lower land and building costs mean higher returns on investment, and there’s a quiet but consistent need for quality housing as remote work and cost-of-living shifts draw people away from cities.

If you ever have questions on landlord software or student housing, I'm a great resource!

It is entirely different than a residential house. 

While I can imagine some cities might be against "boarding houses" or enforce their "brothel law" I can't imagine too many cities would be supportive of it. 

house hacking is great start, that's how i started in the business. would love to connect

Additionally, Airbnb’s policies support hosts when guests do not comply with house rules.

Your realtor will be able to give you a much more detailed market specific answer but with house hacking and a VA loan it should be possible to get 0 out of pocket.