I would go with the '04 and switch out the cam chain tensioner with a hydraulic unit, unless the total cost of that exceeds the '08.
Consider the tire wear on each one too. It'll cost about $400 apiece if you have a dealer replace them.
My .02

What is the price difference in the two bikes your looking at.I'd buy newer with more miles but of course I'm not looking at the bikes.Even better,ride both,which one is the one you'd rather have.There's bound to be a noticable difference somewhere then take your pick!

PS.nobody said the older frames would fold up on you,but an 09 is already 10 yr's.old and there's 09's and above that you can find on the cheap! Just suggestions,which is what you asked for.

Didn't read all the replies but from the few I did read I'd have to agree: get a newer bike with more miles. Even with that, maintenance records matter more to me than miles.

My real will be way different then the other guys I am sure.
TO define a real bike for you-you would have to reveal what you have been on .

To me, an '04 with 30K miles is worth more than an '08 with 60K miles. IMHO, the newer a bike gets, the more "things" Harley added to them that cause problems. I prefer an older bike that's been taken care of over a newer bike with twice the miles. As far as age, Harleys are endlessly repairable or rebuild-able. You can buy a Harley when you're in high school, ride it your whole life, and leave it to your grandchildren when you get too old to ride. I have a friend who bought a 1968 Electra Glide when he was in his early 20's and he still rides it all over the country and he's 62 years old now. He estimates he's put over 200,000 miles on it. Of course, he's had the top end done 3 times, but the bottom end hasn't been touched. He has taken very good care of the bike, and it's beautiful. What are they asking for each bike? You have any pics of both?

I was surfing Craig's List for Harleys the other night, just for shits and giggles. Some of the used bikes with seemingly low mileage appeared to be extremely reasonably priced. Was toying with the idea of picking one up just to get some wrenching time in.

I would think a first real bike would not need any wrenching.
Sounds like you want a real project.
Have you ever worked on a bike B4?

What was the fake bike?

A lot of forums out there if you're looking for a "real" bike. Since you're here, guess that explains it. Would have liked to keep the Guzzi I sold to get my 2000 RK but wasn't able to at the time. That was a real bike for sure. Anyways, I bought my RK with 76k on it. Beautiful condition, PO had recently rebuilt the engine with a SE 95" kit and replaced the problematic FI system with a carb. My first Harley since the '62 Hummer I got in high school, early 70's, and I love it. Works for me, maintenance means more to me than miles do, my 323,000 mile Silverado proves that ! I would get the bike that feels right for you.