You called?

You are right to point out that you've got a bit of loss in the connectors and, more importantly, all that RG58 cable between the footwell and the GSM antenna. In comparison to the woefully inefficient antennas on the hand held mobiles that make up the majority these days, you've still got a pretty decent receive setup, though, although receivers have got better in the years since the telematics was developed.
On the transmit side, yes, you have a higher power class but whether it's fully utilised depends on the cell planning in the area. Since 90% of mobiles are handheld, it's likely that the cell sites have been planned based on their output power. (and I'm talking effective radiated power here, so considering their 2W output AND the very lossy patch antenna on the PCB in the phone).
In urban areas, the cell site planning will therefore probably have been quite tight, and bandwidth is pretty scarce at 900 MHz, so co-channel interference with neighbouring cells might be an issue which prevents the network from commanding 8W units to full power.
Also, it's worth remembering that the signal path has to be reciprocal. The base site will have a
much better receiver and receive antenna, and will most likely be using diversity, so the uplink path is probably going to be a good few db up on the downlink. A BTS can, of course, use much higher transmit power on the downlink but won't do so if the frequency re-use is a bit critical in the area.
GSM doesn't support layered use of other bands and micro/picocells to infill 900 band coverage that well - it was all a bit of an after-thought.
So, go out into the sticks where the GSM900 cells are turned up to cover the largest area possible and you'll have an advantage, but maybe not in more urban areas.
Unless we know details of how the networks plan cells these days (I don't) it's pure speculation, really, but because 8W mobiles are scarce these days, they won't figure highly in network planning and might end up getting neutered to avoid co-channel interference.
Or, in other words, "it depends".
