Yep...stainless is a pain to drill through. Get a nice new set of new cobalt bits to drill through the stainless and use some oil. On the steel support, I would use a titanium bit.
The stainless steel pole cover isn't a kit. Someone brake-formed it to fit over the steel support.
Have you considered offering the customer a new stainless base cover (since someone dented that one up nicely) and a couple of bollards? That stainless is pricey - seems like they would want to protect it.
I assume you'll be applying for the permit, so it'll probably be addressed - but you might want to check the
sign ordinance and make sure you meet any minimum clearance requirements. Some areas get pretty strict with
signs over areas with vehicular access.