Quite a few posts about this, make sure to try a search.
Crispy skin is a function of heat and humidity. Low temp (slow smoking) will not get it for you. Good with the 300 and see if that gets you what you want.
A few tricks are adding oil to the skin, separating the skin from the meat (a good way to get seasoning under the skin and on the meat), and air drying uncovered overnight in the fridge.
This is a fairly common problem with smoked, whole chickens. There are a couple of reasons you are seeing this.
Chicken has a layer of fat beneath the skin. When cooking it at a low temperature (anything below 300º F) the fat is going to render out very slowly. This will keep the meat moist. But, at the same time, it will keep the skin from crisping up.
Letting the chicken dry in the 'fridge overnight will help with any moisture in the skin and give a slightly improved result. But, consider grill roasting (I target 400º F, it's usually done in an hour or so) with wood chips.
You could also take the chicken out of the smoker, let it rest for a bit, cut it up, and stick it under a hot broiler (or grill) to crisp up the skin.
I usually pull my whole chickens after a couple of hours at 250 and finish them in a 400 degree oven. They come out really nice that way, best of both worlds...smoked but with crispy skin!
Another trick is to use turkey skewer, awl, corn cob holder, nail, or whatever to make a whole bunch of small pricks in the skin. Some chinese food cooks even wail on a duck's skin with a stiff wire brush when making crispy duck. This allows the fat to render more easily.
And one more trick that I use when cooking chicken in the oven, although I haven't tried when smoking, is to very lightly dust the bird with cornstarch. When combined with above "piercing" technique it makes a wonderful crispy skin. Almost like fried chicken.
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