Spokes do matter. Trendy, low-spoke-count wheelsets or radially laced wheels tend to rely on stiffer deep-V rims. These are often stated as being the reason for a harsher ride. Your money will be well spent on a set of traditional, 32-spoke, 3X laced wheels. Handbuilt with butted spokes correctly tensioned to a reliable rim, such as a Mavic Open Pro. A 25c or 28c tire can be run at lower PSI than most 23c tires. If your riding style and your frame can accept the slightly wider, lower pressure tire, doing so will add to your comfort. But don't take my word for it. Talk to a few wheelbuilders to see what they'd suggest for you.