Silly questions do not exist - actually, the choice of route question is something many Challengers will have asked themselves.
Yes, it is purely a personal decision, based on your own abilities.
I am with Colin that your mood is a key factor. Looking at the hills in the clouds, I have always said to myself: is it worth it, torrential rain, high winds and NO views?
Only once I have regretted the choice to stay low: when within an hour the clouds lifted and I had blue skies the rest of the day. Nevertheless I had a wonderful day walking through the glens.
I have never done high level routes in the first days of my challenges, and many in the second week. Not only the weather conditions made me decide to stay low, I also need time to get used to the backpacking, to learn to read the Scottish weather again (I lose this ability in the Netherlands), and to get into the mood. That's why I agree with Cameron McNeish that it would be much nicer to walk east to west: when I reach the west coast mountains, I am broken in.
Anyway, these are my reflections on a not so silly question....

Thanks Bart and the others — appreciate it. Am well aware these are personal decisions and I have some experience with elevation in Scotland, although not being from there I have less than others. We’re all making these decisions and there’s different factors we’re taking into account. Was just curious how others who’ve done TGOC make these calls.