Karidne, I spent about $50 going tubeless. You can subtract from that $10 because otherwise I would have had to buy a spare 29" tube. The difference in how it rides is small. If it were just a matter of weight savings, even on the wheels, is it worth $50? For recreational riding, no. For racing or if you just enjoy going fast, probably. I did one race last year for bangs, enjoyed it, and plan to do three this summer. Seeing you are more into racing than I am, depending on your financial sitution, it would probably be a good thing for you. As things go, $50 isn't a huge amount of money to spend in this sport.
That's assuming you can do it for $50 on your bike. I don't know anything about Specialized or your bike other than that they are very popular around here
One thing, though. If you go tubeless, you don't want to have to rely on the LBS to maintain your setup. You need to know how to mount tubeless yourself. So do the conversion yourself. It isn't difficult. Getting the bead to seat enough to hold air using a hand pump is a bit of a black art at first, but not difficult after you do it once. I keep a Schrader adapter in my toolbox so I can use a compressor if I ever need to or am just lazy.
As for new wheels, I am a relative noob, but let me share this. My old bike is a steel '98 Schwinn Mesa weighing in at around 30 lbs. I brought it at a thrift store. It still had its factory tires. I replaced them with tires from the LBS and saved 11 oz per wheel! It rode like a different bike. Pedaled easier, accelerated and stopped easier, handled better, was more responsive. A HUGE difference.
A guy at the race had the same bike I had, a Superfly AL elite, but his had I9 wheels. He let me ride it around the start/finish area, and it was NICE. I'll bet the difference on the trail is substantial. So I plan to spend the $$$ I didn't spend on a carbon frame and get some really nice wheels sometime
. You benefit from more than just weight savings, you know. A good wheelset will be stiffer and the hub will have more engagament points. Also look into thru-bolt if you don't already have thru-axle.