I've never been on a complicated holiday, where booking through travel agents, organising documents and going to busy places like airports are involved. I've just phoned a B&B or a camp site, and since having a motorhome book sites online when I have internet access. I've always been able to drive wherever I'm going that makes it easier too. I don't think I struggle with these things anywhere near as much as many do, but would still find doing much more than this quite stressful. I don't see the point in making complicated arrangements and travelling in stressful ways, as it defeats the object of having a holiday! The farthest "abroad" I've been on holiday is Scotland, including going "overseas" to Skye(!), although I have since emigrated from England to Wales!!!!
So simple arrangements, and simple stress free places to go, is what I look for. And being dog friendly, as I won't go alone!