That would save me money in the short-term but it wouldn't give me anything in the long term. 

What are your short term goals in real estate?

I'd be very confident offering lower than you normally would on these because of that risk added to the fact that materials for repairs will be more expensive in the short term due to lack of supply.Please keep us posted on what you learn and how this works out!

I know a TON of people over here in the Bay Area that own in the south shore area and short term them most of the year.

That is usually short term.You can lend to people who want to hold properties for long term.

If you know the Madison area, that would be good to know in your post.My short background: I currently own 2 duplexes outside of Madison in a desirable suburb but it is also getting quite overpriced.

So I responded to all with a short email saying the property was available and asked that they tell me a little about themselves like employment, timeframe and why they are moving and we could set up a showing.

. :) I am new to the real estate investing world but have learned a lot in a short period of time.

There are ways to invest actively or passively, short term or long term, owning property or just controlling it, being a creditor or a debtor and all of those in various combinations.

With that short of a time horizon don’t stick your money in anything besides a CD or high interest savings account