Re Microsoft, Buddy definitely still has a good working relationship with Microsoft.
A palpable example, it may sound but still very good, can be found in the prospectus, page 39:
Hosting and infrastructure costs refer to the costs of equipment and server time required to deliver the service. Note that as of October 2015, Microsoft is providing Buddy with subsidies equal to the cost of the server and hosting costs incurred.
I think with Dave's connections and his former work, this relationship with Microsoft will only grow.
