Over the decades, we've done it many different ways. As long as your dog is in good hands, I don't think it makes a difference which way you pick. For us, it depended on where we could find the best care, and what life stage we were at - traveling more by air in the U.S. and overseas for career, or lightly here and there to visit people or explore, or now staying within the U.S. as we travel.
We originally boarded them at a couple of kennels, but boy did they punish us (once, we asked the kennel where their old king sized blankets were, and were given a brown paper bag full of what looked like lint, as they'd torn them to shreds). Kitty would always spray in the car on the way home, he was so hopping mad (in a carrier after the first time of that nonsense). My boy Jake the wonder german shorthair climbed right on out of a chain link kennel at one boarding operation (I'd warned the owner & she said she'd put a top on it, but didn't), yep, a 95# dog dashed right up the side and FREEDOM! Gave me such a fright to learn of it, scared the boarding place's owner as well.
Jake could not only climb kennels and ladders, he could open doors both ways (in and out, because we had lever handles). Good grief, even when he had a small seizure at home at 2 am and we rushed him to the Dove Lewis ER, they called me the next morning to say he'd not only recovered, but he'd climbed out of the run, and then proceeded to open quite a few other runs on the way to the emergency exit - at which point they caught him and a few others he'd let out before he went through that door to the street (you know the kind of emergency bar across the door that you just press? Would have been too easy for him). They said come get him now, lol....
So pretty much, our dogs made it as stressful for us on our trips (worried sick every time the danged phone rang while we were away) as it was for them to be boarded, so we took the hint and ended up using a house sitter who lived in and watched the dogs and cat. Yeah, she brought over a boyfriend, and I always expected my freezer to be cleaned out of lean cuisines (it was a stand alone freezer, so that meant quite a bit of food for them). Wore my clothes. But she was good with my animals, even got my cat to a vet in an emergency (recognized it, took care of it while we were unreachable out of the country). I knew her personally as an acquaintance, and that is why crossing the lines happened, but my dogs and cats were thrilled and safe. So I just make a few adjustments in where I kept things and what I put in a safe, and all was well, from my animals perspective, at least.
Fast forward to now where we are semi-retired/work at home, and the dogs go where we go, and if they can't, I just pick somewhere else to go. When we travel, they have a home on wheels with us in our trailer. The only way they wouldn't go with us is if there was an emergency, and I'd probably use the boarding facility at my vet clinic.
I guess my theory is that if you are boarding them, and they don't give a raft of crap for leaving them, then you are doing something wrong
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