We've been a minimum of 8 times. Always planned about 1 year in advance.
Character meals and most popular venues book quickly, months in advance.
The only hotel we've ever stayed at Disney is the Polynesian which is on the monorail line, very nice resort, boat taxi to MK, many perks and it is pricey but for us.. Worth it. Never stayed elsewhere.
Loved the chef Mickey at Contemporary and breakfast at OHana Polynesian for character outings. We did the regular luau at Polynesian.
Taxi from airport ---- straight shot--- not on the free shuttle which can take longer to Disney resorts.... Was about $100 each way and worth it.
We never did dining plans... That's a great way for Disney to make $$$
I worked directly with WDW customer service and always had good results. We bought park passes good from check in through midnight of checkout day... Any park, any time, no limit.
We've stayed in the concierge at Polynesian which has more perks but it is pricey., there was food 24/7 , great accommodations, great views. Concierge is a premium price but you get premium products. Last time we got a private safari at Animal Kingdom which was so overwhelming and super! Each hotel and level of service has perks. We would not have done the concierge when daughter was younger and not able to truly enjoy the perks.
I've heard of websites that get deals and good luck with that.
No matter how you approach it... Disney is expensive.
If you stay off property you still pay parking for the day at a respective park or general location.
We did pay way more to be on the monorail line, however, it was SO easy to run back to the room for a nap, something needed, etc.
Personally... I could stay at the Polynesian or Grand Floridian and never leave the hotel property... It's nice!!
Best wishes to you!!