Its incredibly frustrating that a homeowner can rent their unit out, for a pretty good sum, and not suffer any consequences for non-payment of past dues.

which mind you is not as luxurious as it sounds, as where there is poverty, there is always the darkest sides of humanity, and I only know this because I came from poverty... yes, here in Hawaii... the side they don't share with you on TV and magazines... its tough here for locals sometimes, especially in markets like Hawaii where affordable housing is limited, and the normal market rents are just way too high for single income families.

The next step would be to see if the market can afford new supply. 

Jesse, I feel your frustration here! 

Pretty affordable, but not rent-free either, given that information, is it still worth it for you to live there?

The allure of an appreciating market and job growth sparks our interest, but at the same time, rents in the price ranges we're looking for will bring us a break-even situation at best for the foreseeable future.Then there are the tertiary locations where housing prices are much more affordable, and we could probably acquire doors more quickly, but these markets don't experience the same appreciation.

Since we can't even get a response from the agent, it has been frustrating to say the least.

I can afford to get a brand set of appliances each month in lieu of a person who collects a check and calls contractors as tenants call them. 

We realize it wont be as affordable upfront, but feel like we may have a few less headaches in the southside/intracoastal west parts of town.I've tried to get in contact with some wholesalers to help us find a deal, but I either can't get them to call us back, or they're not willing to work with me since I am partnering with someone else out of Orlando.

As you mentioned you are fresh out of school with limited savings but as an owner occupied rental property owner you can qualify for lower down payment requirements (somewhere between 3.50% - 5%) and the Bank will take into account the anticipated rental income as part of your income so you will most likely be able to afford more than you think.