I can't help you with what your "best bet" would be in purchasing them, because everyone has a different idea about that. I personally signed up for Connections and have not had a problem with them. But then, I remained a member after the trial period. It seems that most of the problem occurs when you try to cancel within the trial period. I believe you can also buy the vouchers through Simple Escapes and also the Hotwire Savings Club. Those are a "pay by month" kind of deal as opposed to Connections yearly membership. Other options are looking at the DIS auctions or on eBay. I think on the DIS auctions you may find the prices nearer to what the face value is.
I have used the Breakfast feature vouchers and feel these are a guaranteed saver if you plan on doing Character Breakfasts. The vouchers cost $17.50, I believe. Character meals are $16.99 for most, and $19.99 for the 2 princess breakfasts. The voucher includes tax and tip, so it works out to be a savings, especially for the Princess ones. Also, its nice to just hand over the vouchers and have it taken care of.
I have also used the Quick and Casual vouchers that cost $11.25. These are good for lunch or dinner at Counter service places. They are a very good deal at the Pepper Market at Coronado Springs and at Beaches and Cream at the Beach Club. At the Pepper Market, we got a steak dinner with baked potato and grilled veggies, a drink and cheesecake for the price of the voucher. This was around a $25 meal (thinking off the top of my head, but you can check out actual prices on
http://www.wdwig.com ) At Beaches and Cream we got the steak sandwich, french fries, coke and the Fudge Mud Slide Sundae for the price of the voucher. This was around a $22 meal. Both of these "counter service places" charge tax and tip. So add that in too. I have heard that people have gotten steak dinners at the All Star food courts with the vouchers and this was a great deal too. But I haven't done that personally. At other counter service places (like ones in the parks), you will probably break even or save a dollar or two per voucher. But maybe the convenience of prepaying your food is worth it. These counter service places don't charge gratuity, so keep that in mind when figuring out prices.
I haven't personally used the Vacation Kingdom Lunch vouchers, so I can't give you our experience. But, Ihave heard these are a phenomenal deal at the Rainforest Cafe at Animal Kingdom.
I have more than paid for my membership to Connections through savings OTHER than my Disney food vouchers. I have given gift cards as gifts (Sunday school teacher Thank you gifts at end of year, teacher Christmas gifts, niece/nephew birthday gifts, sister/brother birthday gifts, etc.) I also purchased $300 worth of Kids R Us gift cards and used that for school shopping. I got a $60 rebate with those KRU cards. So really I spent $240 on school clothes. I have also purchased Kids R Us gift cards to use to buy Christmas gifts. Another $60 rebate for those.
So, there is my experience. We used them last June and had no problem with them and saved a lot of money. We are using them again this Thanksgiving trip.
Maggie