I'm working off a similar playbook, with somewhat more of a bias towards odd jackets as this is more appropriate for my work place.
French blue Lesser tropical suit
Slewfoot brown Fresco suit
Mid-weight mid gray, charcoal and navy PoW 3-piece suits
Two flannel suits, blue/gray spot effect and brown PoW
Two tweed sport coats (stone Donegal, LL blue/brown windowpane)
Fawn houndstooth sport coat
Tan DB Fresco odd coat
On the way this year:
Blue herringbone sport coat
Charcoal SBPL suit with extra stroller trousers
LL RAF blue PoW suit, possibly DB
Olive check summer sports coat
Fox flannel RAF blue windowpane blazersuit.
I've held to solids on the the bespoke items so far and will add some patterns once I feel like I've got a good base to work with.
I do like the idea of having a stroller at some point. Are you going to wear the stroller during the work week or just for weddings, Easter and such?