If I was going on a weekend getaway, sure. But I almost never have to wait a significant amount of time for luggage, and it's usually there when I arrive... because of all the people who think they are saving time by not checking their bags, there are fewer bags to take to baggage claim. Plus I have to wait for everyone to free their oversized carryon from the overhead, that they don't even attempt to dislodge before the aisle in front of them is completely clear. Not waiting for bags is especially true if you have airline status, which should be true for someone who travels multiple times per month, because you get a priority tag.
I did the same when I was young and dumb, going on a work trip to Europe for two weeks out of a carryon, going without some things to save space, doing laundry on the road, hauling my luggage through security, then around the airport, then stuffing it into the overheard, then losing legroom by cramming my laptop bag under the seat, then doing it all in reverse. Hopefully you don't have connections or you have to do it all again. Now I take all the comforts of home, and drop my luggage at the counter, breeze through security, then laugh at everyone who didn't. I particularly love watching people running for tight connections with their luggage in tow, or stressing about finding overhead space to only have it checked to their final destination anyway.
I can't remember the last time I had lost luggage that wasn't an international trip. If an airline does temporarily lose your luggage, they bring it directly to you within ~24 hours. It doesn't matter how far you've ventured from the airport, your luggage appears. Assuming you packed your essentials in your small carryon, this is no inconvinenece what so ever. I just don't see any reason to not check a bag.
Priority tags aren’t a thing w southwest which is a company travel requirement. The companion pass for my wife makes up for it. I’ve checked twice this year and waited at the claim over a half hour twice. Unless it’s a full week trip I use a duffle and can throw my laptop bag inside so I’m carrying one bag. Cant think of a situation where checking it would have done anything but forced me to get to the airport earlier.