Unlike JWM PG, JWM WG is secluded for an apples to apples comparison.
It's a great property.
Elite recognition was fab for me in 2022.
Was there for my wife's birthday.
Since it's cut off from habitation, they try to make you feel at home.
Kempty Falls is built up as a must see.
But keep expectations knee high.
We laughed our lungs out when when got there after much huffing and puffing.
Return trudge will be a challenge with the kid.
Char dukaan, Landour with the famous cake shop etc make for a nice 4-6 hour day trip
But 5 days may be a slight overkill.
3 days may be ideal for you with a kid.
Given where the airport is located, I'd recommend the following
1. Go direct to JWM WG from Jolly Grant
2. 3 Days in JWM PG
3. Day 4 make Dehradun your base (Hyatt Regency there was pretty good)
5. Day 4 or Day 5 do a day trip to Rishikesh (if interested)
Dehardun itself is quite a nice city to explore atleast for a day.
Multiple day trip options too are available.
Made a pal do a similar trip with his wife and two kids in 2023.
I guess he liked it 🙂.
I liked it too, because i got stay nights for his booking !
Helped another pal do something similar with Dehradun as his base.
Alternatively split time between JWM WG and The Westin.
If you are remotely, religiously or spiritually bent, then the area around The Westin may be for you.
PS:
Bear in mind - winding roads, traffic jams, narrow roads and distances...plus the kid angle.
Good luck !