I was far from comfortable the first couple of times I used my compressor on my tanks. Pretty sure it was starfish not eye that was twitching, too.

I have a checklist of the necessary steps to make sure I did everything needed and in the right order which I used the first few times. I found it was good for ensuring no missteps and was helpful towards ingraining the routine.
I have had a 6.8L, a 5L, a 3L and a1.1L Weekender that I've used the compressor on. The two larger are now gone, I found I didn't need anything that big now I could take out the middle man when it came to getting air. The 1.1L I'll pretty much fill, I'll go up to 280/290 on that. The 3L I'll go to about 260/270.
Like you, the 5L I didn't go much past 250 and the 6.8L I only did once anyway, to 240, I think.
The guns I have, only a couple are 250 bar fills and I only go to 230 on them. It's a happy mid-place for me. I think it's a bit of a waste having a 250 bar-capable gun and only juicing it to 200, especially as they are quite big capacity. However, I don't feel the need to push past that 230 mark.
I'm with you on the bottles by the face design but it's not logic to not make the best use of the guns capacity, really. The reality is, if it lets go at 200 or 230, it'll be messy and it's not likely the difference in the extent of the mess will recognisable. In fact, not much affected by the energy release will be recognisable from what it was pre-pop.