If you’re not staying onsite, you can go to guest relations in any park and get special occasion buttons, too. Happy anniversary!
My philosophy on making things special for my 5 year old son was a combination of “free” (well, included in the Disney cost) special stuff, extra-cost stuff, rides, character greets, and pool time.
Pool time was HUGE for DS, even in January, and is one of those things you tend to be resistant to because it’s not Disney-specific but means a lot to kids. It’s a “free” or cost-included thing to do.
On “free” stuff, I highly recommend meeting talking Mickey in MK, it’s a very special character meet that my kiddo loved. For your BF’s son, I would check on getting a “first visit” button at guest services, that’s a free way for him to get smiles and nice greetings from CMs and others. In addition to wearing a button, wearing character-themed shirts is a “free” way for kids to get attention in the parks from CMs and often characters (e.g., DS met Mickey while wearing a Mickey hoodie and got a special reaction from Mickey for his shirt, and his birthday button).
On “free,” too, I think that a well-managed, well-balanced experience that keeps a kiddo active without spending all day in line is a big deal. To that end, I just prioritized one or two character meets per park, or a character meal, because standing in line for character meets is extremely annoying. I also tried to mix up a “line” experience (whether for a character meet or for a headliner ride) with an immediate gratification experience - the shooting arcade, an ice cream cone, something where he was able to avoid having to wait around. I tried to create a balance where there weren’t a lot of back-to-back line-standing experiences, but more mixed activities.
I would plan on budgeting for treats like Mickey-shaped rice krispy treats - some kind of special treat each day, and let him pick it out. Doesn’t have to be expensive. I agree that you can make some meals an experience, too, whether it’s characters or something cool like Sci Fi. However, too many sit-down meals can get annoying for little guys, in our experience, and we found we did very well with more frequent snack-type meals, often shared - cheaper, faster, and more satisfying for DS. Sit-down meals take a LOT of time out of your day that kiddos tend to resist. If you’re going in summer, though, be aware of any options for air-conditioned quickie meals - e.g. ABC Commissary in HS, Columbia Harbor House in MK - because you might all want to eat out of the heat.
I really enjoyed BOG dinner for myself, but it’s probably lost on little boys, though it is fun to meet the Beast. If you feel like you need BOG dinner, maybe look into something like ADR sniper from WDW tools website, it’s $10 to search, but I’ve gotten tons of alerts for options for a trip we booked less than 45 days out, so it might be able to help.
In terms of how to keep your family on a touring plan, I had worried about this but found it to be no biggie at all. First, I also chose “minimize walking” in my plans, so that we weren’t trekking all over the park. Then it was a matter of me “suggesting” something like “why don’t we try out this ride over here.” I’d memorize maybe 2-3 rides/steps on my TP at a time and just direct us to the next one without making a big deal about it. I’d discretely optimize and learn the next few steps while we were disembarking from a ride, taking a bathroom break, etc. There were only a few times that DS had his eye caught by something and wanted to jump ahead to it, and I either went with it or let him know that it was coming up a bit later in our day and we were going to try to hit the next ride on the list to avoid standing in lines.
For your BF’s son’s age group, I would also look into Frontierland’s shooting arcade and Tom Sawyer Island. The dig site at AK would be good. DS LOVED Soarin at Epcot and Agent P. HS was more of a “miss” for us, but signing up for the Jedi Training Academy, if you can, is another “free” special experience.
