I really wanted something that I could use while working away from home and travelling, and which may also be suitable while sailing on Scotland's west coast. I'd considered Blackberry, but thought it too expensive, and it was apparent that whatever system I chose would be a compromise.
First of all, my choice of dongle brand was mainly down to what was available at the time. O2 told me that their dongles hadn't arrived yet, Vodafone would be in the following week, can't remember what Orange said, so it was basically down to a choice between 3 and T-Mobile.
I was put off by the exorbitant claims made by an independent store for 3, so, in the end, opted for T-Mobile, although I had initial doubts about their coverage in the West of Scotland. I signed up for a two year deal for about £15 a month, now £14.67 owing to the cut in VAT. From memory, I can download 3GB per month, but never used anything remotely like that.
I've since used it satisfactorily in many places. Obviously, 3G coverage is very fast, and I've used it for Skype video calls on occasion (but often need to dump the video component for bandwidth reasons). 3G has good coverage in cities and large metropolitan areas; outside of that it gets patchy.
If full 3G is not available, then very often the dongle will pick up something called HSDPA (High-Speed Downlink Data Packet Access) which is usually pretty fast. At worst, GPRS (General Packet Radio Service) comes in at 53.6Kbps, which is adequate for webmail, text based forecasts, even images, but obviously it's a bit on the slow side.
Signals seem to be strongest in open waters where there may be line of sight (or damn near it) to cell transmitters. There are also some places where there are no signals, Balvicar being one. But then there are also anchorages where we cannot pick up Clyde or Stornoway CGs, and Portpatrick Navtex can be patchy in the West. I've quite happily logged to full internet access while sailing down the Sound of Mull, and can get GPRS access to webmail, forums, weather forecasts from the mooring at Dallens Bay.
Incidentally, we have occasionally used the UKHO/RYA plotter CD-ROM with a handheld Garmin GPS connection to a laptop USB connector, while also using the same laptop for email. From memory, to avoid software conflicts, open the GPS/plotter stuff first, and then the dongle; that seems to avoid problems.
Normally there are just the two of us on board, but we both have occasional family and work issues to attend to. Although it wasn't our original intention, we've ended up with access to three different mobile sources, which is probably the best guarantee of access to the wider world. This however may be a serious error, and serious sailors might be better off with no means of external communications whatsoever.

Anyway, it transpires that we now have;
mobile access via Vodafone (for which we also have a Bluetooth <groan> connector somewhere)
mobile access via O2
internet access via T-Mobile
I have been reasonably satisfied with T-Mobile's coverage on the West; but then, I have no benchmark against which to compare it. In terms of UK coverage, sales people will make all sorts of claims, but never seem to be able to show you a map of their own cell coverage, never mind a comparison with their competitors. I'm sure such maps exist - if anyone knows an appropriate URL, please let us all know.
Finally, I've only used the dongle in the UK. There may be some reasonable deal for using the same company abroad, but I've heard horror stories of people ending up with monstrous bills. So I avoid using it abroad.