I'm going to say "brew with the freshest materials you have". If that means AG, go AG. If it means DME or LME, so be it.
The grain at my LHBS is of dubious age since they don't do very much business. The business they do is mainly kits, so their brewer's best kits go really fast (some of the basic LME cans have rust on them they're so old!). In that case, I'd stick with the kits that are fresh. The shop an hour away blows through inventory like gas through a beer drinker, and so you pretty much have the selection of whatever you want, including pouring your own LME.
My 2 cents, as a n00b, is KISS. If you're just getting started, and don't have tons of disposable income, focus on perfecting your brewing technique and rely on established recipes and/or kits to take the worry out of the ingredient assembly. When you can brew a good beer consistently, control the temperature well, and avoid doing silly things like dumping 2 pounds of corn sugar into your beer to "carbonate" it, then you can look to complicate matters more. I figure if you become a good brewer, then the equipment and effort spent on going AG will have better yields. I find if I have 20 things to pay attention to, I forget 5 of them, but if I only have 10 things to remember, I'll tend to remember them all (except tonight, I forgot the f*cking Irish Moss!!!)