That being said, I wanted to ask the community how other San Antonio buy/hold investors are generating leads. 

I'm about to have the lead certificate renewed and the rental certification completed after having done a number of improvements to the property and my question is this: is it possible for me to raise the rent (I'd be looking to raise it to something around $450)?

Do your homework, listen to podcasts, follow these leads and then research. 

Listsource is a great site for generating quality leads.

Annual inspections require condition of property to meet the Housing Authority checklist prior to lease renewal.3.

As they say, the first investment leads to the second and so on!

I've found that a mix of Section 8 [Housing Authority], disability assistance and as mentioned above working class folks.

Any leads would be helpful .

I would rather spend the relatively insignificant (in the grand scheme of things) money on the attorney to tell me I'm good to go, than have things go south a few years in and have regulatory authorities on your case.

I know you will have to work your way through 2-3 levels of customer service before you get to a person with some authority but I would start there.