I have zero background in finance or accounting (I majored in biology) so I need some guidance on these.

The majority of the best properties here have HOAs.

It will depend on the current condition and life expectancy of the property's major components and appliances. 

I am presently paying below market rate for a pretty nice condo in a less than stellar community, so the major motivation for my first house hack is to escape the hood.

You can essentially let a home sit from spring to fall without any major issues coming up due to the weather.

The majority of discrimination complaints are BS.After reading the literature on section 8 it appears as though landlords do not have the option of not accepting section 8 in your state although that dosn't seem right.

Now, out of our 15-20+ deals/mo, we're doing 30-40% flips and passing the rest on without major rehab via wholesale, wholetail, As-is resale, etc.  

It may be helpful to go to the Zoning or Building department/commission, and ask about retrofit status.

Anything else is a major red flag imo.

This is one major reason I always caution people about going with big national marketing companies who don't actually live and work in the markets they sell....but I digress.