You can get rid of a lot of the guesswork on cost right now. Use the website and try all different options to see what the price comes out too. $2500 is going to be tight, I'd try to have a safety net of about 500-1000 more in your pocket just in case.
To help convince him. As a guy who goes there on father/daughter trips, A lot of disney is themed after walts mostly live action from the 50s/60s movies. Some of the newer stuff is really nothing disney at all and more continent or country themed. Even the newer section of MK while dumbo circus themed looks more like the big apple circus pulled up with a dumbo ride than disney. The resorts are resorts and many have some disney touches but they only art of animation is fully themed after disney cartoons. Beaches, Boat rentals, fireworks, pools, resorts of every cost with free for you to use facilities just a quick free bus ride away. Your there long enough that it'll be relaxing to not have to finish a park or see it all. He'll enjoy it more than he thinks.
Some tricks that might help (and I'm also a new jersey resident):
- The value resorts aren't a bad choice if you want to stay on property, I've used them to save money. A tiny bump up from the all stars is the pop century which if the couple extra dollars per night first your budget, I would recommend over it). One year pop was actually lower cost than all stars. Some of the sub-$200 moderate hotels are basically just the value with minor differences and a little more complete in the decorations and landscaping. they aren't always worth double the cost when you hit the standard room and realize it's just a coffee pot different. The food options do vary a little more though so do your research on what works for your style.
- Use
amazon primepantry and gardengrocers to get easy to store food to the hotel. Eat breakfast in your room, you can carry in food to any park. Have cases of water for the cost of 2 bottles from Disney. Skip the meal plan and only have to pay for a few of your meals if your really interested in the restaurants.
- Once you reach 5 days of park tickets, each day in the park is only $10 per person, per day. You can easily add them on from the resort hotel or customer service just outside and park entrance if needed. If not needed, you missed nothing. park hopper is good for your entire stay/14 days whichever is more if you decide this fits your schedule best and worth the cost. Adding more park days on later will include park hopper at the same cost. You most likely will end up splitting up and doing something different for a day or two so you may find out you both don't need more tickets.
- It's cheaper to buy 10ish pictures with photographers or rides than to get memory maker and you can buy them up to 45 days after your first photo is taken from the website to help get you to another pay check at home after. If your going to go nuts with photos and want tons of the automatic on the ride photos, memory maker pre-price is cheaper.
- Meal plans do not include tips/gratuity. A table service where your both getting an appetizer, entree and desert makes that final bill and a fair tip a lot more than you might expect. If your not appetizer or desert people, you can usually save a lot of money unless it's better to spread out the cost of pre trip, during trip paychecks.
- Booking your trip on the website near midnight or overnight is far cheaper than during the day. Prices can vary about 5% since overnight web surfers are rather spontaneous on spending.
- A booking deposit is only 1 night cost of the hotel/room you choose. The rest will be due about 30 days prior to your arrival date. While you wait you can alter your booking for any discount that pops up and any preplanning is not lost. Usually every season has a discount for the next season so around dec/jan you should see some nice room discounts and other things appear. Just change your booking online, compare the before and after and enjoy saving some more money. Also once your signed up on the website, you may get some even better emails on more discounts.
