I'm tending to check bags more often these days. Maybe I'm tempting fate but I rarely have to wait more than a few minutes for bags. Of course, we can each only go on our own experience but I just don't see the long waits often mentioned by HBOers. And I haven't 'lost' a bag in many years - although my personal record was losing the same bag twice on a single day. :grin: But I recognise that could change at any moment.
It's very cool to be unencumbered by baggage and I have a very light down jacket with remarkable pockets that can take a tablet, charger, travel docs and more so I don't always travel with a handbag. It's very liberating.
I'm happy to trade the ease of breezing through security, wandering on to the plane and just sitting down for a few minutes at baggage reclaim. Of course, if I have to carry certain things for work then I have no choice but to haul a bag on board, at which point also checking one becomes a bit pointless.
I also can manage multiple weeks on HBO but it's tedious wearing the same clothes over and I am definitely not interested in spending time finding laundry facilities or hand washing at my destination. If a hotel has laundry then fine, but ultimately I decided I'd rather travel free of baggage, have a choice of gear and wait a few minutes for a checked bag than spend multiples of that time during my trip organising clean clothes.
So in summary, it depends a bit but I do check bags more often than I used to.