I have the above combination - old iPAQ 3660, Navman 3000 Sleeve and the latest TomTom Software. When it works it's fantastic and Tom\Tom is by far the best software I have used for GPS.
However as I say "When it works", it works most of the time but the TomTom software seems to have its setting for reliability set far too high so even though the device is feeding SAT signals happily thru (shown on the the GPS status screen) there can be 4 or 5 or reasonable strength but still not going from grey to red. Setting off from Surrey on a motorway trip it could take ages (realistically 30-60 mins) before it pops up and says' here I am!' Also if it goes unreliable when driving (long tunnel, tree covered route, you can be absolutely done for.
Also I find that if it gets "lost" going along a motorway, it can often only recover itself when you stop or move slowly.
I have checked signal strength etc has nothing to do with car etc .
Surely there is a way to tweak the software or tell it to use the signal it has got - even 4 greay bars look ample for getting a close enough fix.
Have never managed to get a response from TomTom at all
Mark