1. Most likely will go with 240+ channels option?
2. Will use the Special Offer Military & Vets?
Not sure of the question here. The military promotion is a few extra channels that may or may not be included with whatever package you go for, and a free PPV rental every month. Its free, but not exactly a "discount". Other then that go for whatever package you need/calls your attention, and once your 2 year contract expires look into the Flex package. (AT120 is $5 more then Flex as a new customer, so I don't see why not do that then downgrade latter)
3. My son is a Dish subscriber, said there was a "family" discount # for both of us?
Your son needs to contact Dish/go online and ask for/obtain a referral code, and give it to you. This is provided at the moment you sign up. Make sure your account is opened with his referral no mater what, because it becomes a pain to get a unknowing rep to add it after the fact if its not done from the beginning (not more then a few days ago someone else posted about it not being done correctly and having no success after calling in more then enough times). The "discount" is $10 off for 10 months for both of you, I think.
4. I have a brand new roof and do not want a dish antenna connected to it. Is there a metal pole option?
Dish (or anyone in the sat business for that matter afaik) does no longer allow employees to get on a roof, so the dish has to be installed somewhere a ladder can get to. So, a roof install is fairly unlikely unless necessary. Based on your zip code, your locals will come from Orlando, and the satellites you will get service from will be due south-southeast. So anywhere on your property where there is view of this part of the sky, like mounted on the siding or even a balcony, it can go there. Metal poles are an option, although a last resort after roof. If you have your own pole and are able to convince the tech to use it, the mast must be 1 5/8" OD.
5. I also want the Hopper 3 w/2Joey's. See no option to choose that.
You have to call in for that. You will have your credit run, and told what you are eligible for. If you want something you aren't eligible for, or they are pushing you to something else because "you don't need that much" (In other words, they are low on inventory) I believe you can still get it by asking/paying a fee. (Ex. want a H3 but are offered a H2, you may be able to do a H3 for like $50.)
As a person signing up I'm pretty sure you'll have some pretty good leverage, so it shouldn't be a problem.
6 What would be the $, in [detail] for each option/discount etc
You can get this off of dish.com since its the same for the H3 and H2, and is only applicable for the first 2 years, but here it is. Sub total is $105 ($95 with the referral), with the package/equipment you mentioned.
Programing is $90 ($78 Nationals/$12 Locals), minus $5 for autopay, Equipment is $20 ($10 Hopper & $5 per Joey), and whatever state taxes are applicable for FL.
EDIT : I'm really bad at condensing information