Commuting - Bike Recommendation

Here's a tall order: Recommend a bike for a friend who's moving to a beach house for the summer to write a book. (Nice, right?) He wants a bike to get around. (I see an "in" to convert another person to cycling.) Here are his requirements:

1. Not too expensive. He says $400 or less.
2. The bike has to do double duty: He'll want to pick up groceries, but I think he's looking to get back into cycling. Lycra, somewhere in the future, isn't out of the question. He's not averse to drop bars.
3. He'll be riding on paths and roads; no curb-hopping, no off-roading.
4. But he did say $400. (Actually, he said $350!)

Any and all advice is appreciated.

What size? I would say an old Trek road bike would suit him. Most can take racks,fenders and larger tires if need be.

old used steel road bike. he can get one for a lot less than $350 and spend the rest on paper or ink cartridges or something.

I would think a rigid-rigid rockhopper. Eyelets out the wazoo, versatile frame geometry...

I think of $400 as kind of a blackhole price point. Go cheap, get something you don't mind breaking/throwing away, or go expensive, get something that will be really nice, but that middle ground, I don't know... steep enough for buyer's remorse, for sure, possibly not so steep to keep you from just walking away completely, but is there quality there that will keep you running back to the bike for more?

(which is not to say that you can't pay more and still wind up w/ something you hate, but at that point I would think one would have enough invested to figure out what the problem is and motivation to try and redress it).

With all those in mind I keep coming back to the 1990s rigid-rigid rockhopper (http://cgi.ebay.com/Specialized-Rockhopper-Mountain-or-Gravel-Road-Bike_W0QQitemZ230111071089QQcategoryZ98083QQssPageNameZWDVWQQrdZ1QQcmdZViewItem). Of course, that's the basics of what I want, if your friend is more lycra-y, maybe his basics is like a schwinn worldsport (http://cgi.ebay.com/SCHWINN-WORLD-SPORT-12-SPEED-BIKE-NICE-BYCYCLE_W0QQitemZ110109795178QQcategoryZ98083QQssPageNameZWDVWQQrdZ1QQcmdZViewItem).

An older road bike with a decent rack to haul the groceries but lively enough to be fun when he is going to the grocery store. Craig's list should be a good option for this one...

Kona Smoke $349 (http://www.konaworld.com/bikes/2k7/SMOKE/index.html)

A Bianchi Avenue ($349) (http://www.bianchiusa.com/07_avenue.html) seems like it might do the trick.

Might as well bump up to the basic Dew for an extra 50 bucks, though I suppose the Smoke does come with fenders. The Dew would be "livelier" though, no?

Diamondback Transporter (http://www.diamondback.com/items.asp?deptid=20&itemid=228)

Diamondback Transporter (http://www.diamondback.com/items.asp?deptid=20&itemid=228)
That looks cool. The price thing said it could be "between 400 and 700 dollars." Any idea of something more, eh, accurate?

1. Not too expensive. He says $400 or less.
2. The bike has to do double duty: He'll want to pick up groceries, but I think he's looking to get back into cycling. Lycra, somewhere in the future, isn't out of the question. He's not averse to drop bars.
3. He'll be riding on paths and roads; no curb-hopping, no off-roading.
4. But he did say $400. (Actually, he said $350!)

Any and all advice is appreciated.

I would say a good used classic road bike, if he was into road biking previously.

Or a used Giant OCR with a rack.