I have 7 multis, and rarely get noise complaints.

What about purchasing a multi-family property (2-4 units)?  

If you are not prepared to move to a multi plex property to begin your investing you are not ready to invest.

We're looking at single family homes and small multi-family homes, and right now I'm focusing my search on the South Wedge, 19th Ward, and the East Ave/Park Ave area.

My observation from being close to some of these individuals is that there are two main reasons why they often don't invest with other investment managers:1-they don't know them (trust)2-they don't like/know about their track record (competence)Since my current track record in producing returns through RE investing is non-existent, the only currency that I have going for me is my character.

It is a very different animal than investing in single family or multi-family homes.

If you are buying larger multis out of state in up and coming economies and locations instead that is understandable too.

The land bank is looking for qualified purchasors with a successful track record of remodeling homes.  

I'm leaning towards small multi-family.

I think you are on the right track, but it's going to take more networking and talking to more people about what you want to do.