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seb, I don't know the 355 well but a few thoughts anyway.

First re the axle boots - you will have to get under the car (as for all the items) and look at them up-close (maybe drive it on some ramps or driveway kerb or similar). When new the boots will have a soft, pliable lustre and when squeezed won't show any crazing, splitting or perishing. They don't have to be actually "split open" to make replacement necessary - if they show surface cracking when squeezed they should be changed.

Next the tranny. It's unlikely that leaking oil seals will drop the level significantly without also staining the driveway, but again you will need to check around the unit from below, esp where drive shafts exit. Any oil drips hanging from the casing, etc indicate a seal leak of some sort. Try cleaning them up with a rag and rechecking after another day or so. If they come back each day (assuming the car is driven between) they should be attended to, while if the unit stays clean for weeks at a time then I wouldn't bother fixing it yet - all seals leak a little every now & then, depending on car use and climate.
 
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