Depending on the wood, if I'm using a knife a lot, I'd strop it pretty often - it could be as often as every 5-10 minutes. I sharpen the blade less often than that - maybe every few hours of carving, again depending on the wood.
Stropping technique is important - make sure to keep the blade flat to the strop - if you don't you'll actually be dulling the edge with the strop. What do you mean by "chalk"? There are lots of good stropping compounds out there. My favorite is Yellowstone.
But just stropping isn't enough in the long term. You do really need to learn to sharpen if you want to keep that really keen edge. You don't have to go nuts on sharpening gear. A coarse/fine combination India oilstone is plenty good enough.
https://www.amazon.com/Norton-614636855653-8-Inch-Combination-Oilstone/dp/B000XK5ZDY
Other people may swear by a different method, but I've used oilstones for nearly thirty years now, and they work for me. And they're cheap. As a honing oil, I've settled on using lamp oil - I like it because it's cheap, thin, and cuts fast.
You're not going to damage the blade by take a stone to it, but you may dull it until you learn what you're doing. Dull is fixable by ... sharpening. The only way you'd be likely to damage the blade is if you take it to something electric, and don't watch for heat. But you don't need to use anything electric with a knife.
You'll also need a way to repair damage to the blade, which, at least in my experience, eventually happens. For that, a cheap combination diamond block from Harbor Freight will do the trick. Or you could just use coarse wet&dry sandpaper glued to a piece of MDF.
On strops: You don't need to buy a fancy strop. I made my first ones from old leather belts, glued to a piece of scrap wood or MDF. You should have two: One charged with the honing compound of your choice, and one plain leather to follow it and do the final polish.
Amazon has IB8 for 32. https://www.amazon.com/Norton-614636855653-8-Inch-Combination-Oilstone/dp/B000XK5ZDY
Cheapest store deals on Norton Crystolon JB8 and India IB8 for <25$ + shipping. https://www.knifecenter.com/find-the-best/norton%208