I will be arriving in town two weeks before that and I'm wondering if it's possible to propose renting the home for those two weeks.

We renovated our first property, a small 4-unit in Olde Towne East, on our own - it was a very slow process because we both work full time plus have an old dog a home that needs at least one of us to be home every evening. :) It was a great experience, though, and I definitely feel like there is a part of "us" in that building! 

You certainly would want some sort of slush fund for expensive stuff that could go wrong up front but assuming you budget for it, the rental income should pay for the repairs over time once reserves are built up.  

Also is it wrong to talk to more than one realtor, since I'm just starting out and have not built up any working relationships with anyone, to increase the odds of finding more property?

Very close to Louisville, KY and I'm 30 years old.I am currently a computer programmer at a connector company in my home town.

So when I refinance out of a short term loan, there will be a nice chunk of built in equity.

What area of town?

@Marcus Brown  The four towns you've mentioned are where some of the lowest proces in eastern Mass are found. 

These two problems I was luckily in town and got them resolved right away.How do I go about managing these problems in the future/now while I am away?

Also, if you could do it in your college town I would try that too.