I acquired The Proper Car, a SWB W221 S500 back in July 2006 and bought it based on condition and mileage for the price rather than spec. Although I did get lucky with the colour... Flint Grey metallic with a grey over black interior... anything that might get grubby is black and helps break up what would otherwise be a sea of grey.
On the subject of spec, the car is reasonably well optioned from new:
Cornering Bi xenon's.
Upgraded leather.
Heated/ventilated Dynamic front seats.
Harmon Kardon sound system.
Telephone/Bluetooth installation.
Black headliner/A/B/C pillars.
All in all a very nice place to be but missing a few options I would have liked to have... We'll come back to that...
Some background:
I don't think I have owned a single car that I haven't done something to, generally sticking to factory (ish) upgrades, whether it's adding a Ghia X interior to my first car, a 1985 2.3 Granada LX, or replacing the plod interior on my '54 plate Omega estate for a full Elite interior with customised door cards and Irmscher kit/wheels and then subsequently reverting it back to full police spec, lights and siren included

The key to a successful upgrade project is the availability of information, parts and wiring. Nowadays, information is reasonably freely available. For parts and wiring there's a sweet spot of availability around 10-20 years old, (depending on the car), where there are enough around for a choice of used parts and availability of anything else from the manufacturer. So the Granadas were an easy car to work with in the late 90s, and likewise the Omegas until about 5 years ago with a decent inventory of cars being scrapped and dedicated breakers.
My first S Class, aka The Barge, (a '99 W220 S280) whilst not my first Mercedes, was a forced introduction to Canbus systems and fixing some previous bodgery opened up some creative retrofit possibilities. The ABS didn't work because the car thought it had Distronic, (Radar Cruise) fitted... it didn't, and this had to be programmed out of the car. If something can be programmed out, then why can't it be programmed in? That base S280 ended up with cornering Bi xenons, parking sensors front and rear, a different steering wheel and W221 wheels, but the bodywork left alot to be desired so there wasn't much point taking it further.
It's replacement, a '10 R350L, aka The Alabama Mumsybus, didn't escape the upgrade itch. It left the factory with prewiring for rear entertainment. It left me with rear entertainment fitted along with some US only rear stowage bits.
Mercedes retrofits are well documented in their maintenance system WIS, and with a bit of time and effort trawling through the EPC it's pretty straightforward identifying all the parts required for any given retrofit, even if it's not actually an official retrofit item. It doesn't hurt that they have pretty decent long term parts support so getting anything from a nut to a wiring harness for a near 20 year old car is still feasible, and their service item availablity is excellent.