I recently just moved from Reynolds St. in Oakville (just down from the proposed site actually), and although one would expect that there may be opposition to the height of this building, it is important to note that there are other 10+ storey buildings in the area (Allan and Trafalgar).
As for upsetting the residents, some may be angry; however, this part of Oakville has seen recently built condos that are between 6 to 8 storeys (Church and Dunn, I believe). Additionally, 4 to 5 storey buildings line Reynolds with Oakville-Trafalgar Hospital, medical buildings, several offices etc., so I don't see there being huge uproar. Plus, these condos are likely to be high-end, which will keep the old rich people looking to downsize, but stay in DT oakville happy.
And the world of Oakville continues to cater to the rich ...