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I noticed what I assume are railroad tracks between the resturant and the pole. Are they active tracks? If so, this is going to limit your options. You'll have no choice but to use a yagi to bridge to the resturant. Trust me, I've done shipping container ports and having any moving metal containers anywhere near your AP is going to give you major headaches.

If you have to use the Yagi please make sure you have the fresnel clearance to the resturant or else those boxcars will make your life hell.

Please do not use DD-WRT access points. I've been using them for years and I have to reboot them at least once a month. Spend the few extra $$ and get two used Cisco 1200 aps. You can get them for less than $75 now on ebay. They have built in bridging that you'll need to use to be able to bridge from the pole (using a yagi) to the resturant (using an ommi to cover both the bridge signal and also allow for outside coverage). The Cisco/Aironet APs are realiable as hell and can go years without a reboot.

As for a NEMA, it's a no brainer. You have to have one for the pole AP. Since this is in VA, which I've lived in for quite a time, you'll have lots of humity and heat. You'll have to get a cooled NEMA, unless you want to replace the AP after the first summer.

I've done a lot of extreme outdoor installs around the world. Heat (AP killer) and antenna connector moisture has been the biggest problems. Make sure your cable connections are well sealed with good coax sealant tape.