I was on it a month ago and there were definitely two moorings because there were two boats tied up to it. Several weeks ago, however, there was just us and I don't remember seeing a second mooring. It really does vary during the year.
The Chester Poling is one of my all-time favorite dive sites. I've brought hardened New York wreck divers up here who are used to some pretty challenging wrecks down in Long Island Sound and New Jersey, and they absolutely loved it. It's in excellent condition, sits upright, and they don't get much easier to navigate, I'll tell you that!
My first dive on the Poling was in February of 2002, and the only way I knew I had made it to the wreck was when I hit it...vis was absolutely abysmal - maybe 3 or 4 feet tops and incredibly dark. I would have been almost completely lost had it not been for a dive light.
Not 2 full months later, in April of that year, I was on that wreck for some of the best visibility conditions I've ever seen in Cape Ann: at least 60-70'. We did our safety stops at 15' in full view of the deck. You could back away from the Poling far enough to see the wreck's entire sillhouette. Unbelievable. On this dive, I didn't need the light at all, even to look inside the wreck's portholes.
On average, I have found the Poling to host 15-20' of vis during the year. There's no reason you should feel encumbered by taking a good dive light, so I say go for it. I think we'd all agree that on some level, you'll find use for it. In most situations on that wreck, however, your eyes will adjust within minutes and there should be no need for a light for navigational purposes.
I've dove the Poling probably 2 dozen times and each time it gets easier and easier, but I never dive it without a modicum of respect. A dive shop that I teach extensively for has a policy - instituted by the owner - of not allowing AOW students on the wreck. Beyond the depth and current you can find on there, I think the biggest thing to keep vigiliant of is trawler nets and fishing line that get hung up on the wreck with varying degrees of bulk.
My personal feeling is that if you treat the Chester Poling with the same respect you would any other advanced New England dive, you'll have a blast. When it was intact and in good shape, I think the Poling/Nina T charter was one of the best days of diving you could have up here.
Have fun, and keep an eye out for the lumpfish who lives on the deck!