I am leaning towards getting the TiW card - even though we are new AP holders
This trip we will be traveling with me, my husband and our 22 and 24 year-old daughters - we will be staying on property for 7 days - the last 4 at club level. Between the 4 of us if we order 2 rounds of drinks at parks, etc per day while sticking to places on the discount list - the card is paid for - that is before food, etc. Major caveat is that we have 4 legal drinkers- I don't know if it would be worthwhile for just myself and husband. Plus, it is coupled with the fact that a lot of the AP discounts expire after 9/30 - and our next AP trip will most likely be in October or later
Another perk is that our AP year will expire before our TiW year and we will most likely be back and without an AP before TiW expires for us
If we buy in June
SOUNDS like TIW would be good for you - I'll add a couple of personal comments:
One of the biggest Highway Robbery moves (with YOU as the Highwayman) is to employ TIW at Fine Dining Restaurants. SIGS tend to return the most total dollar payback. Simple math really.... 20% on a $500 total bill = $100. 20% on a $100 total bill =$20.
Now - I have to get into tipping (sorry Mod).... that 20% is pretty much paying for a decent tip. If you choose to NOT tip? The discount pretty much vanishes. Just us - Sandy and I can't behave that way. So TIW, for us, is a Robin Hood Act..... we steal from the Bill, and give it to the staff

. We would have given them 20% anyway -hence, we see value

.
IF one plans regular vacations (as in every 6 months, our case) - a carefully purchased TIW will cover THREE trips. If this is you? CALL TIW - those folks will actually work with you to tell you WHEN to buy a card, based on your trip schedule, to maximize the system for all it is worth

. The TIW folks are absolutely WONDERFUL. They WILL tell you if it is a mistake to buy a card one week earlier than you planned.
Side benefit: CALLING and ORDERING a TIW card will give you a mailed PLASTIC card. Sandy and I have lost count of how many times Restaurant staff have said "A hard stock Card? THANK YOU! The Paper ones cause nothing but trouble - how did you get this?".
All personal opinion - I'm not necessarily right, no one else is necessarily wrong.