Date registered: Jan 2013
Vehicle: 65 220SEb, 97 SL500, 98 E320 Wagon, 2002 ML500 - former W108/W112/W114/W123/W124/W126/W140/W220
Location: Tampa, FL
Mentioned: 14 Post(s)
Quoted: 1052 Post(s)
To address your original question a lot depends on where you're located.
Ideally, the peak of the market for convertibles is usually in mid spring, like April or even May. People are starting to get outside more, and the desire to "cut loose" and enjoy improving weather is greatest.
That's if you live north of the Mason-Dixon Line.
If you live in the south, or southwest, southern California, there is still somewhat of a seasonal thing to the market, but it's far less pronounced since the conditions are ideal for a convertible pretty much year round.
As for what you've got in the car, forget it. Prices on the R129 models have been soft for years, and continue to be so, unless they're a unique model like a Silver Star or Anniversary Edition, and/or have very low mileage.
With minimal information that's supplied, I would guess that if this car was in good condition you might be able to net between $6,000 and $8,000 depending on a number of factors.
As for the maintenance and repairs, you've just gotten hit with a number of items that were coming due at the same time. Few, if any of them will need to be done again for a long time. These aren't high maintenance cars - much of what you've done sounds like deferred maintenance that needed to be caught up, not ongoing repairs that will continue to occur on a regular basis.
This is a situation many of us have entered into depending on the age and mileage of the cars when we bought them. You either bite the bullet and do the work, then enjoy the car for many trouble free miles after, or you dump it and take a beating, while the next owner enjoys the fruits of your labors.