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The 1/2 acre lot would be in an older subdivision but really close to businesses. I'm afraid they may knock the trees down close-by for commercial. If that happens, our new home may be exposed to it. I don't want to be sitting in my living room looking accross the street at Walmart. It ahs plenty of trees around now, but with things growing, you never know. The house we are in now, we built new 4 years ago. We are really glad we did that b/c we new nothing would need replacing. The only thing is the neighborhood has some houses that aren't kept up with, but the neighbors are great. mmm
...and second many of the things in Frogandtoad's post.
While it does take time and effort to update an older home, the end result will be just the way you want it, not someone else's idea of nice.
And when I read that the newer home might end up being exposed to commercial building... EEEEE!!! Run for the hills!
You can always change the house, but you can't change the location. And 1988 isn't that old. I'm a model '68 and still feel like a kid The house we bought is also a '68 model and we're in the process of redoing everything. But it's what we wanted. We wanted mature trees, space, character. Okay, the character we really wanted was Trinity Park, but that just wasn't to be. Some days we work on the house, some days we don't. We've learned to live with the construction clutter and our friends don't mind coming to our chaos. At least not as long as the wine is flowing....
Brass may be hideous, but it's nothing compared to our current master bath. But just wait until we've finished the remodel. It's going to be the most beautiful 15 sq.ft. bathroom in Durham Meanwhile, I've found that I get just as clean in the icky bathroom. Since we plan on living here for some time, I figure it's worth the wait.
Definitely go for location. I have lived in an 80 year old house, a 7 year old house, and a brand new house. The best thing about brand new is that the systems are all in working order, the roof is new, etc. We also built the brand new custom--REAL custom, not "pick from these 10 plans we do" but designed by us, top to bottom. That's the best. But our location wasn't ideal and that's a real drawback.
you could go for the older home and ask the seller to pay for a home warranty, and then renew it each year. That way you're not hit hard if the a/c goes out. And factor in any non-cosmetic repairs that the inspector comes up with, like a new roof or hot water heater, that sort of thing.
1988....was that around the time they were plumbing with those "bad" pipes??? Just get a really good inspector. My husband and I are NOT handy and do NOT have time/money/patience to mess around with renovations and stuff. If you are, older is a great option.
The first house we bought was 50 years old in a lovely subdivision in fairfax county, va. Great lot, super location, with tons of mature trees and a very solid house (all brick, built to last). We did have to upgrade a lot of things though and the rooms were a bit small for our needs. I'm not complaining because we doubled our money on it when we sold up to move to the triangle . Our second house was a 2 year old tract home in wake forest. Although the floorplan was great, the lot sucked due to annoying neighbor in close proximity (pot smoking, dog-pooping-in-yard, firework-crazy POS neighbor). Also the house proved to be a junker (I won't name the builder in case I get sued). Our third house, which we built new recently, has proved to be house I like the best. Mainly because we got to choose a great lot. Treeline in the backyard (yes a permanent one, the trees are part of our lot ). It's nice having new and not having to worry about too much maintenance. However, I do miss that 50 year old home sometimes. It had a lot of character. My two cents is to buy the older home on the nicer lot if you are going to be there for a while and are willing to spend time fixing it up.
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I'd go with the older home
The house we bought is also a '68 model and we're in the process of redoing everything. But it's what we wanted. We wanted mature trees, space, character. Okay, the character we really wanted was Trinity Park, but that just wasn't to be. Some days we work on the house, some days we don't. We've learned to live with the construction clutter and our friends don't mind coming to our chaos. At least not as long as the wine is flowing.... 
