I have two Sec 8 properties in Del City... they were a pain in the @$$ to fill in the past, due to the extra set of inspections the city would require--and they would nitpick like you would not believe. 

Looking for anything really, but primarily, where could better process, systems, or tools help?

It's a pain.

@Richard SinghI feel your pain! 

Big banks are large, bureaucratic, and slow to make decisions, which made short sales drawn out and painful.

Not at all, but sharp landlords that understand tenants won't say anything bad about them besides factual stuff like paying rent on time.Also, if they haven't been there at the current landlord very long, call the prior landlord.  

Does SLS not think it's a short sale. is that why it's a pain?

Sounds like you may be dealing with a “professional” tenant that could be a pain for many years to come.

He also said that it might create a lot of pain for a new investor like me since the HOA might harass me even though they may not be able to fine me legally.

I'm a bit more reckless and willing to take some pain to learn.