From my experience (from a few years back but still appears to be the case) is that Wind River is just wrapping Yocto these days. There could be value for some orgs where they don't have engineering teams if they do a contracting arrangement but I think, generally, orgs are better building directly on Yocto (or BuildRoot) without a vendor in the middle (other than your SoC vendor and their support layers). I'd save your money and pay for a seasoned embedded linux expert or three if you are maintained a connected product.

For smaller deployments, I think it makes more sense to look into solutions like mender.io, etc. for updates/fleet mgmt/etc.