As i research more on ride quality/performance etc, i realize how much farther the worm hole goes. I understand that tire/rim choice can make a HUGE difference on the comfort of a ride over longer distances etc. But how does one identify such characteristics without having to spend $$$$$ riding each set of wheels 40+ miles? Obviously extreme example is going to be some 50mm aero rims vs some Mavic Aksiums the aksiums are going to ride 'smoother' (less harsh).

How do i go about choosing a comfort and performance set of wheels for different types of rides

If you ride hills go for lighter weight, as long as the wheels are strong enough for the load and road conditions. Comfort has a lot more to do with tires than rims.

+1 A couple pounds of pressure difference in the tire is going to affect the "smoothness" of the ride more than the wheel. Choose wheels based on the cost/durability/weight/aerodynamics spectrum.

Your weight is the determining factor in wheel weight. If you are a 190 or higher you should have a 36 hole slightly heavier rimed wheel.
The tire size is determined by the bike. Many of the so called racing bikes can't clear anything over 25mm wide.
Tire rolling resistance is determined by tire flexibility and proper pressure.
https://www.adventurecycling.org/res...SIRX_Heine.pdf

I'm not sure I totally agree with davidad on the need for 36 spoke wheels. I'm easily over 200 lbs with riding gear and a backpack on me. But not by much. I've ridden 32 spoke wheels for years now with no issues towards reliability or durability.

For ease of self maintanence stick with regular style spokes and spoke counts. No minimal or grouped spoke boutique wheels. Just good builds with 28 front and 32 spoke rear for unloaded riding with higher spoke count wheels for bigger loads.

Most of my own riding is stop and go sort of city rides. For this use light weight at the rim and tire will easily be felt as a bike that sprints to speed from a start a lot easier. From personal experience the lighter the rim and tire the more you'll feel like you're wearing a big Superman S on your shirt or jersey. But if a lot of your riding will be done on country roads where you ride for longer distances with none of the block by block stopn'go of city riding then the deeper dish streamline wheels may serve you well if you can keep up the sort of speed that makes their streamlining beneficial.

Light is always nice, but not at the cost of breakages along the road. (unless if you're competing, when a lighter wheel might be the difference between a podium finish or not. If you feel that a DNF is same, same as finishing in the pack, this might be an option)

Earlier posters make good points about traditional builds and the importance of tire pressure.
The precise number of spokes needed is hard to determine. Between build quality and riding style there's a huge space for varying experiences.
(ignoring differences in build quality) A cautious but heavy cyclist, good at going light and staying on nice surfaces can get away with a lot of things which would leave a lighter cyclist with a harsher ride stranded along the roadside.

But the main thing is that as long as you stay away from spontaneously taco-ing wheels and clearance issues everything else (with the possible exception of disc wheels) will still be rideable. The performance curve is a smooth hump rather than a sharp peak, so whatever you get will still be useable.