The newer hose/fitting is definitely stiffer than the older ringed type, but I have not really had any trouble with it, especially going on too far or to easily? I have had the newer ones for about a year and a half and it really hasn't gotten any easier, like I thought it would. I use it a lot and I disconnect the hose and plug-it every time I set it down.
Same as Rick Herrick, I was initially concerned about the connection to the dust port/tube, but having owned one for over 7 years, it was never a problem.