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Welcome. I can help you with the first three questions.
(1) would a 2004 coupe come from the factory with the fleece or paper filter?
It came with paper and I am still using original paper filters.
(2) if you only drive 4,000 miles a year is a once a year oil change sufficient?
Synthetic oil doesn't break down so changing the oil once a year if you don't exceed 4,000 miles is okay. I store my car so I change the oil when I store it and then again if I reach 5,000 miles before it goes into storage again. This is probably excessive and doesn't need to be change as often as I do but I am a little obsessive.
(3) will Chrysler roadside assistance cover towing due to a flat tire (customer service has not given a straight answer on this yet)?
The answer is no, tires are not covered by Chrysler only by the tire manufacture.
(4) what is the usual life expectancy on the all-season continentals?
Sorry I can't help you with this one my car came with the Michelin Pilots and so far I have 15K on them and they still look good. I will definitely replace them again with the Michelin's.
You didn't say whether you have bought one yet or not. If you did congratulations and if not what are you waiting for?