Looking at a 2008 4S (cab) with 26k miles. Seems in very nice shape and CarFax shows routine maintenance (drive belts at 15k, tires, and front crankshaft oil seal and driveshaft seal replaced at 21k).

I have had a 2006 Cayman (21k miles) before this and it shifted so smooth.

Took this car out and it seems fine but I do notice a little (hard to describe) - notchiness - going into second. It does slide in pretty nice just not as smooth as other gear. It doesn't grind or noisy, etc. I seem to recall 2nd gear always get the brunt for manual shifts.
I didn't take the car out that long.. maybe 20 minutes so maybe it wasn't warm?

Sorry to be vague - but just curious as to any thoughts.

Thx!

 

Some folks have a problem getting into first gear on occasion with these cars. This is normal. Additionally, my understanding is that first and second have steel rather than brass synchros for first and second gears and this may affect how they feel when shifting. Finally these are balk type synchronizers and will feel a bit clunky compared to those found in many Japanese cars. A crunching second gear or a gear that pops out when decelerating indicates worn synchros. Sorry not to be more definitive in my answer.

 

+1 to Fahrer's description. Drive the car again and get the trans fully warmed up. 1st and 2nd should then be smooth. If not, then you have worn synchros.

 

When was the last time the car's brake and clutch hydraulic fluid was flushed and bled?

My experience with my Boxster is if this fluid is not flushed/bled on "schedule" (2 years) shifting problems can arise that are really due to the clutch not functioning 100%. In the case of my car no matter how careful I was there was some "crunching" (of the mild sort, but totally out of character) when shifting. It was like I was not depressing the clutch all the way but I was. There was no room left between the pedal and the floor. There can be clutch issues too, for instance the car can be difficult to move from a stop smoothly, no matter how attentive one is to this.