I’m currently in the process of searching for my first property, which I hope to house hack and eventually convert into a long-term rental. 

Once converted to a rental, repairs and improvements may qualify as deductible expenses, but pre-conversion repairs typically do not.

I don't know your area, so I can only write to my experiences in PA.You don't really convert your property to Section 8 (S8), but rather sign a lease with a tenant who happens to be funded by S8.

Hi BP community,I'm going through a landlord's worst nightmare now, long story short, I have a fully furnished rental property in Florida, previously an AirBnB converted to long term rental. 

Quote from @Joshua Land: Look to learn, and hopefully implement converting my duplex into an assisted living center.

This defers capital gains and depreciation recapture taxes on the sale of your fourplex.After converting it into your primary residence, you may qualify for the primary residence capital gains exclusion ($250K single/$500K married), but only for appreciation after the conversion; gains from the rental period remain taxable.

Then have a 6 month period to convert all old currency $20 and $100 to new currency.  

Did you check for houses on the auction list,  or you can check with banks and look for REOs and convert that into a single family home and house hack or turn it into a Airbnb. 

During the "fix up" process, you would use a different kind of loan that will end up converting to a DSCR loan once you have tenants living in the unit(s).

He should read his mortgage and see what it says about renting and/or converting to rental.