1k below? Get any WM6.1 phone which fits your budget. They should be capable of running all your pdf and office files. your other specific Criteria s are met too.

get an IPhone 3gs. Fits all your needs

5800 fits your budget. I'm not being funny but my colleague (who's actually 60++) uses one. It's cheap and user friendly from his point of view. Not to mention it would make him look tech savvy using a touch screen phone.

is a 3.5mm audio a must or you're perfectly fine with fast port?

Often the drop of WIFI connection is due to the unstable router. It happens when it need to communicate alot of pc at one go and has been running for a long time.

Triple kill!!!

J/k. Yeah it's kinda lame for the joke.

GPS without data charges, stick with Garmin with Malsingmaps. You can get them free. There are a few contenders. n97, 5800 etc from nokia devices. If you don't mind, you may try out some Windows mobile devices. I find them much tailored towards power users. HTC devices.

Iphones would recommend data plan as it draws data out from google. Conversely there are dedicated turn based apps but then again, I still think malsingmaps running under garmin works best. Not sure. Maybe I'm wrong on this.

don't worry. They won't be hunting you down they just giggles in their seats

To ts, you may want to check out on nexus one. This device offers a better hardware. Made by htc. The camera is better than hd2. Since HD 2 is plagued by the pinky issue.