He doesn't have to worry about a rough needing replaced or a tenant causing $20k in damages after one year living in property.  

I am not sure if anyone else saw it:"Full and Liquidated Damages": This limits both parties to just the damages stated in the contract.

When looking into it, the basement had water damage that didn't worry us since we knew how to remodel that area ourselves.

The crash caused significant structural damage, and the driver fled the scene, later reporting the vehicle stolen.

Further, long-term upward pressures on inflation remain, and will cause the Fed to be cautious with interest rates. 

Needs all new cabintry, windows, doors, roof (has some life left), fixtures, fencing, some electrical and plumbing changes, and some framing/drywall due to termite damaged sill plate in areas.

Small details like a handrail on stairs or window locks can cause your unit to fail an inspection, delaying the start of rent payments.

Quote from @Khaled El Dorry: I have a portfolio of 3 SFH's (2 in Jax and 1 in ocala) and 1 duplex in port charlotte (never flooded or damaged due to hurricanes) that have done very well for me.  

It depends on a lot of factors; primarily the local jurisdiction rules that may limit lease changes (in Portland/Oregon rent, security deposit, screening fees, an no-cause evictions are heavily regulated).

Despite the risk of losing their Section 8 status, tenants rarely pay their share.There is likely to be significant damage caused by Section 8 tenants.