I have had it rented out since July 2018 and have had a great property manager handle everything since. 

How is maintenance handled and what specific info is shared with owner & when?

@Kermaury MusgroveInvesting out of state can have it's challenges and extra costs like travel, bad people, unexpected repairs.

This is not the way to handle the situation.

I'm mainly concerned right now with how to handle this with my taxes. 

I have a management company handling my houses and I have not missed a rent payment from section 8 in years.

Hey Liad - Condos can pose some challenges mostly due to monthly association fees, limited control over the property, and potential for slower appreciation compared to single-family homes.

I did a search on zillow both for multifamily (<200k) and older homes (<150k) in Alabama, most of them look pretty creepy, I am kinda new, not sure if I can handle those.

A lot of manpower is lost.As we approach our busy section 8 season (for us April - July) I am looking for better ways (more affordable and efficient options to the investors bottom line) to plan for and execute the workload which may include hiring someone that has section 8 experience to handle our CHA inspections(and associated maintenance work) or a company that we can outsource when the weeks get slammed with inspections. 

Challenges?