We're staying at POP.
I'm just a little concerned because I see tons of people here talking about making ADRs at 180 days out and we're going in less than 3 months. Also, DH is being a pain in the rear about making an itinerary. He hates to make plans yet will admit that we've had some boring vacations in the past due to not making any plans.
He also insists that we spend one day outside of WDW to do stuff in Orlando and the surrounding area. Again I'm

because we went to Orlando 2 years ago and did a few touristy things like Sea World, some go-kart tracks and the outlet malls. Beyond those things, we were bored to death. I have no idea what he thinks we will do that day (and neither does he at this point).
First off welcome to DIS! Second off, breathe in breathe out it will be a great trip no matter what.
Easy part first, the day outside of WDW - List of 10 thngs to do:
I'm going to take that to mean NO PARKS. There is a lot to do outside of the parks, but still at Disney. If you've been recently bored with an Orlando trip try these non park things at Disney:
1. You'll get a voucher for discounted Minigolf use that; if you play Fantasia Gardens grab a meal at Beaches & Cream, they don't take ADRs and the focus should be on your ice cream dessert there. The other course is closer to Downtown Disney.
2. Downtown Disney - you mentioned shopping, there is plenty there as well as restaurants (no ADRs at some); you'll also have a Planet Hollywood $15 Voucher, you could use it on a meal, appetizer or dessert stop there(not valid on alcohol)
3. Waterparks - Disney has 2 fantasic parks, pick one and have a blast
4. Doesn't sound like you're golfers (ie. you didn't mention it on the last Orlando trip) but Disney has 4 awesome courses
5. Go see LaNouba, the Cirque de Souliel show in Downtown Disney
6. House of Blues is a restaurant which can include live music, check hob.com to see the schedule during your stay
7. Tour the resorts - Just hop a bus, boat, monorail and go check out other Disney resorts, we peeped in the Poly, Wilderness Lodge, Animal Kingdom Lodge, Contemporary on our visit (we stayed at Caribbean Beach resort) We spent a rain delay in the game room at the Wilderness Lodge!
8. Just laze at the pool at Pop, not as elaborate as some of those resorts I mentioned, but downtime at the pool has its advantages
9. Horseback riding at Fort Wilderness campground (make reservations

I know, I know!) There is a buffet at the campground which you may have success getting in w/o a ressie, especially for lunch maybe dinner too.
10. If you'll have a rental car (I think they are a waste at Disney; onsite transportation is free, Disney Magical Express to and from the airport, I don't need to spend the time getting, returning or filling up the car) head over to Universal Studios City Walk, restaurants, clubs and street entertainment makes it a fun atmosphere, free parking after 6pm
Now back to the food and ADRs
You will need them if you plan to eat at each of them during your trip. They are some of the most popular. Coral Reef was the hardest ADR to get for our trip last September. We ended up with a lunch that worked out great for us after a full and early morning start at the Magic Kingdom. It as easy to hop the monorail over to Epcot for lunch. Treat those meals as destinations or attractions unto themselves. Biergarten and Coral Reef definitely deserve that distinction. LeCellier doesn't have "entertainment" value, but many really simply love the food there.
You would have enough time for a nice Disney dinner on your arrival night. Make an ADR for 8pm or later and you should even have time to freshen up or cat nap beforehand. Just chose a restaurant at a resort or Downtown Disney so you don't waste a park admission just to eat. We did that and thought it was a great way to kick off our vacation. Otherwise you can get a good meal at the food court at Pop.
It would be helpful to decide what park you'll visit each day. Then you can try to get ADRs at a place in/near that park. All of the places you mentioned are in Epcot so if you eat at each you'll spend a lot of time in Epcot, which is just fine.
Here is some info that may help you plan:
The Magic Kingdom will be open late (past 11pm) on May 11th, so you could have one of your dinners at Epcot that day, enjoy Illuminations then take the monorail over to MK for more fun that night.
Epcot will stay open (past 9pm) on May 9th and Disney HS will do the same on May 12th. Again you could have dinner in Epcot and take the bus to the Hollywood Studios for the late night activities.
You can enter the Animal Kingdom at 8am on May 12th and the Hollywood Studios on May 9th (your first morning at Disney).
You don't have to use any of these extra hours, but they are a privledge granted to all resort guest,s so why not use the perk a time or two?
Planning your Disney trip should be fun, hope this takes some of the strain away. There were many here on the boards who helped me last year so just trying to "pay it forward".
