Council is, in Oakville fashion, indifferent with regards to transit. Transit isn't of interest this term. It's always just that thing they send money to year over year to get people to GO trains and do their part on the environment. It is the fact that Oakville Transit isn't really that important, that OT doesn't receive the funds and long-term support it needs to grow.
For YEARS, Oakville Transit's key goal has been to, someday, have 15-min or better frequency across the network, and work towards a grid (not really possible but okay). Unfortunately, Oakville Transit is always more or less told by the Town, 'do the best you can with what you have'. Essentially, Oakville Transit does have a lot of great, grand ideas.... But the planning is based on what OT has, as oppose to what they SHOULD get. This has consistently stiffled progress. Aforementioned in addition to poor ridership stats year over year, the Town thinks of Oakville Transit as more of an appendage than a tool.
For the time being, Oakville Transit is trying, but your observations are correct. The lack of 'how to' is greatly out stripping ambitions. Essentially, over promising, and under performing. This, leading to a cycle of further neglect and criticism. It's NOT Oakville Transit's fault, but unfortunately it isn't anyone's solution either.