I would consider myself a WDW vet, though I haven't been there since FP+ was implemented in 2013. Can't help you there. But I'll help you where I can.
Resorts
Definitely stay on-site at WDW. Deluxe's are usually very expensive (like DLH or GCH). I've stayed at all the moderates at once at AllStar Movies. I'll never stay at a Value hotel again after that stay. Mods are really good. Decently priced, much better bus-to-park service than Values, and are very unique in theming. Coronado is my fave (not a bad section there), followed by French Quarter, Caribbean Beach, and Riverside.
Dining
The Dining package is kinda cool to get as it allows you to not worry about price when you go to order. It's a voucher system based on meal, not money. And if they offer the free dining plan, go for that. The
DDP gives you a snack, quick service meal, and table service meal for each night you stay. This sounds like a lot of food, but WDW is definitely better than DL in this category. Here's some of my table service favorites that you can get dining reservations for:
MK: Liberty Tree Tavern, Tony's Town Square Italian, Crystal Palace (charter meals with 100 Acre Wood gang)
Epcot: Teppen Edo, Akershus, Le Cellier (2 credits), and Biergarten
Hollywood Studios: Fantasmic Dinner Package at Hollywood&Vine, SciFi Diner (foods OK but experience is cool)
Animal Kingdom: Tusker House for character lunch w/Donald and the 4 others (Flame Tree BBQ is the best quick service meal at WDW)
Contemporary: Chef Mickey's character dinner (get this as soon as possible)
You will feel the Disney bubble at WDW if you stay at a Disney resort. It's just magical all the time. And it's so big, your subliminal mind knows that the big city isn't just on the other side of the gate. The parks are dropped in the middle of Florida forest and grassland, so it really feels like an escape. You'll love it.