I'm saying that quad-shielding is over-kill, not worth spending the extra money for.
It won't hurt, but it offers no benefit in an OTA application.
If I was able to pay $15 less for the 500' reel of standard (non-quad) wire, that's the route I would go.
I'm currently working through a 50 pack of connectors, (# 92-650, Home Depot SKU 373290). I've used other brands such as Paladin in the past and have had no problems with either.
I've been using a kit like this for several years now,
http://www.amazon.com/DataShark-7001...shark+coax+kit
For sealing connections exposed to the weather, I use a tight layer of Scotch 2228 sealing tape, protected from sun light with a layer of good black UV resistant vinyl electrical tape (Scotch 88T is great if you can find it for a fair price).