Welcome to the forum.
The most important thing to consider is the condition and maintenance history of the vehicle. It matters little if it's a 420SEL or a 560SEL provided you find a vehicle with no rust and one that has been properly maintained. It's well worth spending a few thousand more up front for a pristine example than to find a cheap one with little or no records.
Since you are not thorougly familiar with them, it's worthwhile to have a proper inspection done by a knowledgable shop. The gassers have issues with their timing chains at certain mileage levels and it's rather costly to change them.
Because you live in Canada, the diesel would probably not be the best choice for you unless fuel economy is of primary concern and you can put up with the issues of a diesel. However, again, if a pristine example happens to show up with maintenance records........due consideration should be given.
The 300 SEL is a good vehicle, but, it has issues with 4K rpm running speed on the highway that some folks cannot stand and it starts in second gear which is a bit too tall for the six cylinder. You may find it underpowered if you tend to push a vehicle. It does provide slightly better fuel economy than its gasoline powered bretheren.
Remember this well when looking at these vehicles.......especially when one encounters a low selling price:
There is nothing more expensive than a cheap Mercedes-Benz.
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