Is it worth upgrading to an entry level carbon wheelset if I already have pretty light wheels? I wouldn't be saving much in weight but there's the aero benefits to consider. Would be interested in hearing any personal experiences.
As @dolph mentioned above it is totally worth it but also depends on how much you actually willing to spend. Ksyrium's cost is close to some good Elite/Tagoola wheelsets.
Is there a resource you guys recommend when looking at how to spec a wheelset? I've gone into the individual wheel threads and there seems to be lots of details and terms I'm not familiar with (rim width, spoke options, hub options, hub reliability, etc.).
It depends on what you want to have - custom built wheelset or comething ready to use? If latter, the budget-to mid segment is saturated with pretty decent options. Look for the complete build with steel spokes (pillar 1420 is a good starting point), DT Swiss clone (almost every brand has its 240 ratchet clone since the patent is void but skip hubs with excessively large number of ratchet teeth) and modern int/ext width (23/31 mm is the absolute minimum IMO). You will feel the biggest effect in regards of responsiveness (from carbon as a material) and rim width (superior grip, flat protection and cornering due to the bigger air volume inside of the rim).
I do not recommend custom build if you are not willing to geek up about hubs.