Usually in the year following your purchase, the property appraiser will reevaluate the house based on the new sales price.  

@Tanner KingWhen I analyze a house hack deal, I focus on metrics like GRM, Cap Rate, Cash Flow, House Hack Savings, and Future Rent Potential.

Good on your friend for suggesting house hacking a duplex.

We had a house on the Deschutes River in the subdivision we were doing a spec new construction house in.

If I sell one house per year, it will pay for itself.

You'll typically need to set up your account and get familiar with the process of working with the local housing authority.

I'd also send it registered mail or deliver it to the house yourself. 

Get a house in a great neighborhood during the summer 2025 and sell my primary in spring 2026.

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.

I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.