I'm currently a CFI grinding out my hours for a regional gig, but my life long goal is to earn a slot for the Air Guard. Anyone here who can give me some pointers? I'm sitting around 500TT and currently no degree (planning on using my ratings to knock some credits off).

Is your dad a Guard Pilot, or General?

That's the only sure way to guarantee a slot.

I'm sure you already know this, but you'll need your degree if you want to be a pilot in the air guard (unless you want to fly those remote control thingies, but I'm guessing that's not what you meant).  The interesting thing with the guard (or reserve for that matter) is that each unit is different.  Some units give pilot slots out to current members only, some only do local/hometown guys, others want to see some other qualification (lawyer, medical, etc) which will make you competitive.  

If I was in your spot, I'd start looking for a unit that I'd want to join, starting with local places first.  You can go to www.guardreservejobs.com/newjobboard to look for current openings.  Then, knock out your bachelors degree.  You'll need to start pilot training prior to your 30th birthday (though, waivers have been granted to start later, but that's generally been a pain in the ass).

Some things to consider...most units are looking for guys that will stay with the unit.  They don't want to train you up then you leave for another unit.  Or, for that matter just get hours then get an airline job then bounce.  They're generally looking for guys that will stay in the unit for a career.

Thanks for the advice, I'm about to start knocking out my degree, and I'm pretty young so age isn't an issue. Is it common at all for guys to move to an area specifically for the Guard, or is that kind of looked down upon?

I don't know if it's common, but I'd say it's not out of the ordinary.  I definitely don't think it's looked down upon.  A former Marine buddy of mine got hired by an F15 guard unit.  They mandated that if he wanted the job, he had to live within 50 miles, so he moved there.  There might be some issues in some states with members of the state guard not being citizens/residents of that state, though I haven't heard of any.  When it comes to pay, when you're on orders, the units will pay your travel and per diem (standard drill days don't pay travel or per diem), so there is some added cost to the unit for hiring an out of town guy.  (With a local guy, there's no travel and you stay at home, so there's no per diem)

When it comes down to it, if you're application is pretty much equal to another guy's and the unit only has one UPT slot that they can fill, they'll 9 times out of 10 hire the local guy.

Maybe back when the F-101 was new...  I was hired into a fighter squadron and not a single person in my family had served in the Guard or reached a rank above E-5 in any military service.  I recently sat on a hiring board where one of the applicants fathers was a retired pilot from the squadron...he didn't get hired.  My squadron places a lot of emphasis on guys who are currently serving in the Wing and many of us were prior enlisted, at our base.  Having said that, we have hired plenty of, "off the street guys."  

Get to working on your degree.  When you get within a 1-2 years of graduating, knock out the AFOQT and TBAS (google them), and start calling up bases and asking to come up for drill weekend.  DO NOT waste your time talking with the recruiters, they have no bearing on our pilot hiring process.  Find the base operator number and ask to talk with a pilot in OPS.  Tell them you're interested in applying for a pilot slot and ask to come to drill.  Visit the squadron MULTIPLE times, hang out at the bar after flying, converse with the pilots.  Don't be over bearing and try to wow them with your 500 hours, many never flew light GA and couldn't care less.  We just want to get to know you and see if you're someone we're ok with being "stuck" with for the next 20 years.  

Best of luck!

Realize that the military doesn't value hours and ratings the same way a civilian job is going to.  Basically beyond 200 hours and an instrument rating, they don't care about your aviation achievements.

So, your college work and other "whole person" stuff is going to be just as, if not more, important than your flying experience.

Third all the advice above about calling units, visiting them on their drill days, hanging out and getting to know unit members socially.  The "pledge" process is ultimately going to be the most important part of getting the call to interview.

Awesome advice straight from the horses mouth as it were.

The Guard track has always fascinated me, because it's the Best track that nobody ever knows about, until they're already in the business.   I've made it a point to ask every Guard pilot I've ever flown with, how they got in.  Out of at least 87, a small handful said they transitioned from an enlisted position.   The vast majority had serious inside connections.  I met one girl who almost got a slot, but failed the medical.    As RW said, it is possible to crack the code, If you are a natural networker and willing take the initiative.