Due to our occupations, we are free to travel anytime of the yea
If you are, I'd consider a trip in either January (minus Martin Luther King weekend), early February. late August, or September. Less crowds and prices tend to be lower too (but not always so price out several different sets of dates!)
If I learned anything, it was that I'm not happy being cheap with vacations
Love this, absolutely true for me as well. Back when my husband and I were dating, we went to WDW for two weeks (also did Universal, SeaWorld, and Kennedy Space Center). We stayed at my mom's time share to save money, and while it was a great resort, like you, I learned that there are just certain things I will not go cheap on, and vacations is one of them. I'd much rather go less often and do everything we want as opposed to going much more often and having to skimp. There's also a lot of things in our everyday lives that we'd rather not have or do so that we can afford to travel to some sort of Disney destination about once a year.
OP, since you're planning your trip out relatively far in advance, you may want to start some sort of savings plan. If you use a credit card, you may want to see if your offers airline mile rewards (or if you'd be interested in opening one that does- but beware, you must pay your balance off in full each month or else the interest you pay will quickly outweigh any cash back rewards). If you do not like to use credit cards, as a pp said, switching to a cash only budget (no debit cards, just pull out cash when you need to buy something) and using the $5 savings plan is also a great way to save.
All Star Sports is my husband's favorite value resort- so great choice! If you aren't already, sign up for Disney World's emails so you will get an email if/when they offer deals for your time frame. The dining plan isn't usually a good value for most people, so like someone else said, if you happen to go when they offer a choice between free dining and a room only discount, I'd take the room discount unless you are someone who orders appetizers, sodas, desserts, etc with every meal.
Definitely pack snacks (and alcohol, if you desire) in your checked bags and bring them with you for snacks. My husband and I find that eating a small breakfast at the food court (often sharing a platter), then bringing granola bars and other snacks in the parks can sustain us until around 4, when we have a large dinner.
Table service meals can quickly get expensive, but perhaps if you follow advice of previous posters and ask for Disney gift cards from friends and family for holidays and birthdays, you could swing a few. The nice thing about Disney is on their own website they have many menus WITH prices posted, so you can see what's in your budget ahead of time. If you can't find it on Disney's website, a quick google search can help you find some prices. The buffets usually don't have prices listed, but they are very expensive, FYI.
A few of our favorite budget friendly TS meals are The Plaza in MK, Kona Cafe at the Polynesian for breakfast (famous for their Tonga Toast), and Sci Fi Dine in Theater in Hollywood Studios. (But remember- "budget friendly" at Disney is different than budget friendly in the real world).
here's to hoping this trip ends in an engagement EEEEEEEEE)!
Crossing my fingers for ya!