Good on your friend for suggesting house hacking a duplex.

I agree with John, we are seeing renovation costs of $150k- $200k for a basement unit and $250k + for a coach house. 

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

I saw once where a developer gave the buyer a pass on paying HOA fees till a house was built on a lot. 

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

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

I would keep rent a little below market, then split the monthly bill between the tenants on top of rent.Old houses in cold climates get expensive in the winter.

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

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.

Quote from @Edreco Amos: Quote from @Rob Drum: I’ve owned a condo and Tampa, and two houses down the west coast of Florida the last two years.