I have a set of Vuelta XRP Pro wheels that came on my old bike. They have treated me well but they are heavy (specs say 2021 grams without skewers/tires). I broke a spoke on the rear and replaced it and it will not go 100% true. I have had a mechanic true it. It's ride able but there is a slight wobble still. But they are $150 wheelset and maybe time to cut my losses. I just upgraded my frameset and was going to wait to save money for a better wheelset so if I upgrade now my budget would be $500 max. If I wait maybe 6 months I could spend $1000. but I have a older CAAD9 frame so not sure how much I should really throw into wheels.

For example I was looking at something like this:

Reynolds Solitude SE Road Wheelset - Road Bike Wheels / Wheelsets

Would that be a decent step up from my current wheels

Reynolds Solitude SE Road Wheelset - Road Bike Wheels / Wheelsets

Do a search - there's been wheels threads at just about every price point over the winter/spring.

Depending on price and luck you can look into:

Vuelta Corsa Lite or SuperLite
Fulcrum Racing 5 (frequently available new/used as a take-off from an expensive bike), the 2014 Racing 5's are about 80g lighter than older versions.
Shimano WH-6800

Bicycle Wheel Warehouse Blackset Race is a good value if you're not overly concerned about looks. The set is around 1490 grams. Loud hubs - but I kinda like loud hubs. Handbuilt and remarkably true out of the box. Race build is just under $500. Been riding them for about 9 months and no problems yet.

Unless you are looking for race wheels I don't think you will find much noticeable improvement in $1000 wheels vs $500. The extra money mostly goes for aerodynamics or weight savings and neither is going to gain you more than ~1 minute in an hour of riding.

You don't need to spend $1k. $650 gets you a Boyd Altamont set which would be a good all around wheel.

Altamont alloy clincher - Boyd Cycling

If your looking at the solitudes try to find a set of the 13's. 27mm deep and weight 1575. I picked a set up on ebay for 300 shipped with an ultegra 12-23 cassette.

Good, used sets of Rolf Prima Elans can regularly be had for less than $500 on eBay. They are some of the lightest production clinchers you can find (sub 1400 grams), and amazingly quick / responsive. I've bought three sets now for my various bikes, put Grand Prix 4000s tires on all of them, and find myself not wanting to ride anything else.