I'll start this by saying that I'm a Kenwood fan...
For that mic connector on the head/body thingy, I find that having the mic connect to the body of the radio is more convenient. It allows for mounting the head in places where having a mic-cord dangling would be very inconvenient. The typical mic-cord from Kenwood is longer than 'normal', that eases some of the stretching problem. If it can't stretch far enough, it only takes a typical telephone extension doo-hicky to make the cord longer (Kenwood offers such a thing but home-brewing it isn't difficult at all).
I've found that Kenwood's programming/menu methods are more intuitive, simpler than the other manufacturer's menu structures. (That 'KISS' thingy was made with me in mind!)
Long squelch-tails? I personally think they are useless and aggravating. Talk to the repeater owners. That goes for those 'roger beeps' too. (That's one of those 'personal preferences' thingys, suit yourself.)
There are 'work-arounds' for almost any 'feature' of any brand of radios. May not be the simplest/easiest things to do, but they are possible. If the other characteristics of a particular radio fit your needs well, then a 'work-around' or two isn't all that much of a problem. The absolute best advice I can think of is 'try before you buy'. That's also one of the hardest things to do though, ain't it? Oh well. Another little bit of advice that really does make things easier is don't let "analysis paralysis" hang you up for very long. The best choice for a particular situation always depends on the situation and will change with the situation. I've found what works for me, now it's your turn...
- 'Doc