If you want to get started in real estate investing then I'd highly recommend buying the newest fourplex you can find in an ideal location.  

I'd have to agree with Sam, house hacking is great, but also starting out with a rental that you'd live in is ideal.

Do you think they see which one has the best reputation, customer service, which counter clerk is the nicest?

Multi units prefer 2+ bedroom units, 1,000+ square feet each unit, side by side is ideal if possible, want at least electric and gas separate, any area can work for these as long as it isn't a D area, but usually B-C class works best since buying these primarily for cash flow.

Ideally, I'd like to replace the whole thing, but there are alot of issues with the placement of the heating and condenser units and whether there is enough ventilation.

Also, when is it ideal to be issued?

The likelihood of the credit card company siding with you is unlikely (they are going to side with their customer 99% of the time) but it is free and worth a try.  

I think ideally we are seeking tenants that are a part of the college town workforce as you mentioned. 

Real Estate IS a customer service business.

These are often ideal for long-distance investors, who what to work with an established team that manages all aspects of your investment.