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You are at a very interesting price point. At $1000, you could start affording carbon clinchers as well as tubulars. You could probably also afford specific tubeless wheels. Try to decide what you want most - tubulars have the most potential of weight savings and softer ride, tubeless is younger, but great potential with excellent but heavier ride, clinchers are ultimate convenience but can be heavier though very durable.

I highly recommend direct to consumer companies Williams and ROL. Both have very affordable clincher and tubular models and have EXCELLENT customer service. I personally ride Williams system 19's, 1430 g, laced to hutchinson fusion 2 tubeless tires (290g) with Stan's conversion kit. Very light, very strong, and very comfortable combination for MSRP way below your $1000. ($500 wheelset, $150 for 2 tires and tubeless conversion).

Remember to budget for quality tires, tubulars can definitely be more expensive, and technically much more difficult to mount.
 
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