Mountain bike wheel and tire suggestions?

If your bike is as "old school" as you say it probably isn't disc brake compatible. Also your forks probably will not allow any other size than 26" wheels and tires. You can search www.nashbar.com.
If you are unfamiliar with wheels, tires, and cogsets your best bet may be to bring your bike to the nearest bike shop. It may cost a bit more but it will be done right.

Not a pic of my bike, but same model.



Cannondale Killer V 2000 is what I have.

I may just bring it in.

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honestly you will probably be better off buying a used bike

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Truth. I have a 25 year old rockhopper I ride 4 to 5 days a week. A while back I researched upgrading components and I quickly realized that buying a new/used bike was a much better option. Upgrading piece by piece is not cost effective.

I need to upgrade and will likely buy used when I do. If we ever get past covid and folks quit trying to be healthy, you should see the market flooded with used bikes, workout crap, etc.

IF you have an old school bike, get a used copy of this book.

Zinn & the Art of Mountain Bike Maintenance

It will basically tell you everything you need to know about working on the bike.

In order to mount disc brakes, your bike will need to have the mounting posts on the front fork and rear triangle. Post a couple of pics of your front and rear tires/frame and we can tell you if it's possible. They help with stopping power and hand fatigue, but I rode for years without them.

Edit: The bike in the above pics doesn't have the posts required to mount disc brakes. You're stuck with calipers.

Now, to the question that you originally asked, what wheels tires to put on them. First you have to make sure you have the clearance for any tires you might put on. Look on your rims. They should have a sticker with a number on them. Something like 26x2.0 or 26x1.75. The lower the second number, the skinnier the tire. If you can't find it on the wheels given the age of the bike look on the tires that are on their now. Typically, for "cross country riding" you're looking at a tire that's between 1.9 and 2.25 or 2.3. A decent MTB tire for general use will cost between $20-$40. When I was riding alot more, I really like the Panaracer Fires. But at your skill level, you won't really notice a big difference in the performance level of the tires right now. Also, as a causal rider, don't get wire rimmed tires. They can be hard to get on/off if you get a flat.

Good luck.

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On tires, should I go tubeless? These seem easy to repair.

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It’s actually the opposite. Tubeless is less prone to get a flat , especially pinch flats. But once you do get a flat from a puncture , you will have a mess on your hands and will need a new tire and also sealant to put back into the tire. It’s even harder to seat, you need a big burst of air usually to get it to seat. That being said, i would still run tubeless, you can use a tube in it to get you home. Pack some extra wipes because sealant will be everywhere while installing tube.

Probably not going to replace it. This bike has sentimental value. I had the same model since college until it was stolen last year. I understand it will cost more to customize, but I'm ok with that.

26" ain't dead, but new parts are hard to find.

Check out Pinkbike. I have bought and sold tons of parts and bikes on there. They have great online community.

In the buy sell section you'll find wheels and many other parts (tires included) with lots of filtering options to make it easy for you to navigate.

Pay with PayPal to protect yourself, but I've bought and sold thousands of dollars of equipment on there with no issues.

Pay attention to spacing and dropouts. You're most likely using QR dropouts with an older bike like that, which are more and more rare to find.

Tires, similar to wheels, will be hard to find but try to run maxxis or schwalbe. I run Maxxis Ikons on my fast bike.

I always recommend tubeless. It reduces weight and allows for running lower pressures, but it takes a little maintenance and the correct setup to be worth it.

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You can buy a front shock/fork that will allow you to put on cable pull front disc brakes

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My original bike had a custom front shock / fork.

Are disc brakes a necessity? I saw the poster above's comment...but if I just want to keep the old style brakes, I should be good?

I have a decent amount of hills but nothing too crazy.

Forgot to mention if you need new wheels/rims it will probably cost you about $200 for a used set. Good used sets of 26" wheels are really hard to find. Honestly that $200 would be better served getting put towards a new bike. Even 7-8 year old bike would be an order of magnitude upgrade over that bike. And this is coming form a guy that loves to restore and use those old 90's bikes.