My trick for avoiding getting the knitted gloves stick on the velcro of the outer gloves is to put both outers on before doing up the velcro on either. A well placed thumb allows the first finger to put some leverage through the loop to pull the cuff across. It isn’t necessary to pull the cuff all the way across to get a good seal, indeed it can’t be if you’re wearing thick layers such as a Gabba. I agree the velcro does seem unnecessarily grippy but I haven’t had any problem with the stitching giving way.
The silk inners do wear quite quickly but then I found the same thing skiing with silk inners and they are not hugely expensive to replace. My knitted gloves and outers are holding up well after a couple of years. I was a bit concerned they wouldn’t be grippy or padded enough but they are fine.
I agree they are probably best suited to road use but I wear mine off road too in cold weather. But speaking of the cold, no they are not “deep winter” gloves.