We have done both. Honestly, it's that third child that was our tipping point. The extra cost for onsite accommodations pushed us to look off site. I admit I was that person who was convinced that staying offsite was going to destroy our vacation. Yet, back in the day when child number three arrived we became a one family income. It was either off site or no WDW. So I booked an offsite condo whimpering and crying about it for months before we arrived. Well, not only did I survive, but I actually found there were many things I liked better about offsite condo stays. So much so that now that our income has thankfully increased and our trips are no longer controlled by budget I often still book offsite condos. We love the space! I'm also not about cooking and cleaning on vacation. Yet, the ability to have a full size fridge with our crew (three teens) is a huge cost saver. We keep it stocked with easy make your own/clean up your own meals and snacks. Having an in room washer & dryer is so very nice and eliminates the need to bring tons of luggage. When we do a week long condo stay with park tickets for 5 Disney Adults, parking, gas and food (we mostly eat out both on and off site) our typical budget is between $2500-$3000. We do drive so we have our own vehicle so admittedly our transportation budget is low.
There have been a few times in the past few years where it has made more sense for us to stay on site and we decided the premium cost was worth it to us. Most notable this past March for Spring Break. My eldest was in his a freshmen year of college, our middle child was taking four AP classes in his junior year of High School, and our youngest was taking three High School classes while in middle school. There was no way anyone was missing school for a weeks travel last year. In addition two of our children are athletes which require summers to be all about sports. We basically were left with either traveling to WDW Christmas or Spring Break. We knew it would be super crowded either set of dates we traveled. Being seasoned WDW vets we also knew fast passes and ADR's would need to be booked ASAP. We also considered that traffic and crowds all over Orlando are nuts both sets of dates. With this in mind we opted to stay on site for earlier fast pass bookings, early/late extra hours in the parks, transportation to and from the parks and easier ADR bookings. We also, decided to splurge and stay in two rooms at AKL and get the dining plan. We usually, don't do the
DDP but we knew were were not planning on venturing off site and with three older children who could tour the parks without my husband and I the ease of the DDP connected to the kids Magic Bands appealed to us. We did price it out and we could have saved about $1700-$2500 if we either stayed in one room at Riverside or 2 value Room but we elected to stay at a nicer resort. Our total price for this package was a bit over $7500 for the week. *We are Florida residents so park tickets and rooms discounts did apply. Also, for some weird reason AKL offered a better discount on a FL Resident rate than the mods or values did for our dates of travel.
Basically, for us the decision to stay on or off site comes down to what is going to work best in our given situation of that particular trip. Yet, I can honestly say we have had fabulous vacations in both settings. Condo stays are so very nice to have space and many offer great amenities if you do your research. Full discloser, I don't think I could handle a week of all five of us in one standard hotel room and one bathroom ever. I also know I would more then likely pick an offsite condo over the two value resort rooms my family requires at Disney. We did consider renting DVC points for our onsite stay but we were unable to get availability for our dates during Spring Break last year. In the past when considering DVC rentals for the difference in price an off site condo appealed more to us. I absolutely loved everything about last years onsite AKL resort stay but it came with a hefty price tag. By comparison, this year we are doing a family 7 day cruise on Royal Caribbean Allure of the Seas and a week in an offsite condo in Windsor Hills the last two weeks of May for about the same price as our weeks stay at AKL last year. *We did get heavily discounted cruise rates and a great deal on a condo by being able to travel in low season this years as apposed to high season last year.
I suggest you nail down your dates of travel weigh the pros and cons and figure out what works best for your families situation.