NM, We have done it several times in the last few years. We have stayed at Disney Resorts and also Hotels around WDW.
I highly recommend staying in a WDW Moderate resort, which are closer to WDW than the WDW Value resorts. The Moderate hotels, we have stayed in Coronado Springs and Disneys Port Orleans French Quarter resort. The benefits as you mentioned transfers on the Disney bus, which your 10yr old we love. The Disney resort shuttles and also the new Fastpass + band now when you stay at a Disney resort. you can pre book your
fast pass rides up to 60days prior to arrival and 30 days if your not staying on resort...
Also what we did we pre-ordered from an online grocer in Orlando and had our groceries delivered along with water bottles for our stay of 8 days. We also bought a cheap microwave and left it in the room, (a generous tip for housekeeping).
Chain owned properties are ok and can be better value and more luxurious, but when you factor in things like Extra Magic Hours in the mornings or late closing, the chain hotel shuttles don't always cater for this, we found out the hard way last year. We stayed off property and the hotel shuttle from WDW did not extend its hours for guests who stayed late at Magic Kingdom special late night closing. Also the shuttles run by hotel chains don't have the extended routing to various Parks. For eg., they will drop off you off at Magic Kingdom Transport Centre and from there you have to work out the best way you are going to say for eg., Epcot for the day Keep this in mind and if you are going in Orlando summer, think of the humidity and heat. Its a killer and after half a day you just want to jump on a Disney bus and go cool down in your room go for a swim, and then go back for the evening. Easy and you don't have to think..
Happy to answer any more questions you might have. I was brief but could have written an essay. We are veterans of WDW..
Trying to remember the on-line grocer we used they are very popular over there and do this all time. Our groceries were waiting for us at concierge when we checked in, you tell them approx. when you are arriving and they get your groceries to you around the same time you are checking in. Just remembered so here is a link
https://www.gardengrocer.com/