I do agree that the interface is clumsy at times. There is a little too much work to move around to where one wants to be, and that is a shame. I'ts not hard, just a bit irritating. As a long time 106 user, I can definitely relate to what you are saying Joey, I was just curious as to the exact nature of your problem.
There is a trade-off here for sure. I feel the 800 has better audio, some cool features, and is much more modern looking (for those who that matters for), but the trusty 500 (106) is a simple and reliable workhorse. Personally, the superior audio alone make the difference. My 106 has to be maxed nearly to work in a loud car situation. For myself, in given geographical areas, I pretty much leave one scan set active and occasionally take a scan list off of that scan set, or add one, so the whole interface is workable.
For sure the 800 is not a milair scanner! But then again neither is the 106, and that is why I keep a Pro-43 and a BC780 around to this very day. Some things were done best 15-20 years ago.