On my Home edition machines, it's easily more than 3 times a year.
Windows is my daily driver too, and while I generally like Windows, the two things I hate the most are the updates and how bad the search is for launching apps (I know some people are going to chime in and say search is fine, but if you have a lot of apps installed, it can be laughably bad).
The search is absolutely terrible. And it's inconsistent. Sometimes I can type "no" and it'll come up with Notepad++ immediately. Other times I have to get all the way to the first + before it finds it. And still other times, it can't find it at all. That goes for all programs too, not just Notepad++.
I've somewhat tried using tools like Everything [0] but never given them more than a few tries before uninstalling. Maybe I should do it again.
I started using it in the WinXP days, stopped during Win7, (never used win8), and Win10 regressed in this department so badly I've returned to using this ancient software...
I've tried a bunch of stuff too, and even bought one (Listary), but from a muscle memory perspective, nothing beats hitting the Windows key with my pinky. I guess I could remap the Windows key, but I think that would have too many negative side effects.
I was on Mac as my daily driver for about a decade (but have no desire to go back), and Spotlight worked great as a launcher.
I think the variation in experiences is the variation of people with Cortana on. With Cortana on, I've never had a bad experience with app search in Windows 10. Using machines (such as work laptop) with Cortana off there are some very weird moments where search just stalls out that it shouldn't.
I think there are two trends that should help:
1) In Insider builds for the upcoming 19H1 release (round about March) they split app/local-machine search from Cortana UX again, and it's getting a lot more standalone testing because of that. (Pushing Cortana back more to the core voice search / assistant focus.)
2) Microsoft is in the early stages of the process of a big Bing "Enterprise" / "Cortana for Business" push. That may also help reduce some of the search differences between consumer uses of Windows and enterprise uses of Windows.
My problems have been less with stalling out, than horribly bad guesses at what I'm looking for.
Sometimes it correctly figures out a misspelling, but most of the time it doesn't. Sometimes it won't find a multiword application name unless you type in the first few characters of the first word of the application name. Sometimes you can type in the correct name, and it just pretends the app doesn't exist at all.
Considering that MS makes a search engine and Apple does not, it's suprising how much better Spotlight is at launching apps (I used to get 95+% accurate guess rate) than the Windows Start Search thingamabob is.
Indeed my main laptop is on Pro.
Btw I agree that the start menu search is unimaginably bad. Insane how so many gigahertzes can be wasted so much.
I'd upgrade my Home edition PC's to Pro, but for the features that I would benefit from (better update behaviour, remote desktop), it's not worth the expense to me. To upgrade an existing license from Home to Pro costs almost the same as buying a new Pro license.