It was definitely much easier to retain, because it meant you qualified the next season. Pre-1999 much of the challenge was qualifying for it in the first place. Once you were in it was obviously far easier. A fraction of the teams to compete against.
Sorry but not having that logic under any circumstances given they've never gone ahead without the holders. The only time where the rules stated it should happen they caved and let Liverpool back in, thereafter changing the rules. And this is ignoring the fact it's been
easier for sides from the countries where the winners tend to come from to qualify since they changed it up.
Unless I've completely misread you, I mean my next point will tell you if I have...
My old man was a big advocate of 'Champions only' for a long time, but at the same time when I was a kid would tell me that sometimes he felt the UEFA Cup was the harder trophy to win, because the champions of any given nation could go to pot the following season (e.g. Leeds in 92) whereas with 3 or 4 teams that were the next best, there's a good chance of coming up against the best sides in Europe in that competition.
I don't think he was going as far to say it was the harder to win, but there was logic there. And now the Champions League has that same logic, e.g. 2013 you had prank English champions under Moyes, but City/Chelsea/Arsenal were all still good sides (though probably not in Europe that season, so bad example, but you see my point).
Ultimately I just think it's one of them. Going to Eastern Europe and knowing a bad night could send you out of the competition in October carries a lot more pressure than being able to absorb a loss because you have five more group games, but the higher volume of good sides probably does swing it in favour of Halsey's argument. I just don't think it's cut and dry.