I was browsing Costco.com today and came across this TomTom here for $250 after $100 instant off:
Costco - $100 Off TomTom ONE XL-S 4.3" Touch Screen Display
Without researching, I'm sure you can find it slightly cheaper elsewhere but for $250, you get Text-To-Speech, a 4.3" screen, and it's a TomTom. My wife and I just purchased a Garmin C330 from Sam's Club as a gift for $130+tax, but it's a very basic GPS and nowhere near as nice as my Nuvi 660 or the TomTom One XL-S for that matter. So compared to what we just bought as a gift, the TomTom seems like a pretty decent deal for what you're getting.
As far as map updates, they aren't usually free. Garmin wants $80 for the upgrade to the NT City Navigator 2008. I was able to get Garmin to send me the new map because by my procrastination, I never registered my Nuvi when I first got it last Xmas. I didn't register it until this past September, and in the process, I was able to lie on my registration the date I purchased it. And since I inputted a very recent date, I automatically qualified for the free map update.
I highly suggest buying a GPS from Costco or Sam's, especially Costco as you cannot beat their return policy. Costco has an unconditional return policy on most items, excluding some electronics like TVs, Cameras, Ipods, and computers. Sam's Club return policy on the other hand is a bit more up in the air, as I've talked to their CS and they say they will take a return at any time, but then they also offer extended warranties at an extra cost, which makes me believe their return policy is not like Costco's. In any case, you can easily return it to both places without having to pay a restocking fee.
Other stores will charge a 10 or 15% restocking fee if you return it and the unit is not defective. In other words, no buyer's remorse unless you want to lose money. That's to prevent people from buying a GPS, using it for their weekend trip, and returning it the following week.
If you have a sibling(s) or relative(s) that wants to get in on this gift and don't mind splitting the costs for a more expensive unit, another thing I would HIGHLY recommend is getting a unit with Bluetooth. I'm not a traveler so I really have no need for my GPS for most places I go, but I find myself bringing the GPS just for the bluetooth feature alone on my Nuvi. I could care less about FM transmitter, MP3 player, JPEG viewers, videos, traffic updates, Text-To-Speech, etc. They could take away all those features and I wouldn't miss them, but I would not want to be without Bluetooth. This is from someone who barely uses his cell phone, so for someone that is constantly on the phone they will love this feature even more.
The POI databases aren't completely accurate so sometimes before I go out for drive to a place, I will look them up in the GPS. With the BT feature, once I find the POI, I can hit the call button and it dials the store. I can find out if they're actually still in business, what their store hours are, etc. There's a company called "Parrot" I believe that sells standalone BT units that's comparable to the BT you'll find in your navigation, and they want more than $250 for something that ONLY does BT, so when you consider that the prices of GPS w/ bluetooth isn't so bad.
Another recommendation is to get a friction mount for your car ($30-$40). If you get a Nuvi, it's a necessity as their suction mount is JUNK. That thing WILL fail on you in a couple of months. With the friction mount (think of a non-slip bean bag), you can easily hide your GPS from view when you're not in the car. Even if you detach your GPS, anyone looking to break into your car can see that you own a GPS if they see a suction mount on your windshield. If you have your GPS on you, they'll have broken into your car and stolen whatever they want. Or if you don't, they will find your GPS in your glove compartment and stolen whatever else they want.