I think people have you on the right path Richard...
It's my home stomp as well, so I'll throw out my own perspective -
As some have inferred, where to go and what to do totally depends on what you're looking for...but no matter what - it'll be busy. The 2 week charter doesn't give you quite enough time to hit that real 'solitude' which you can find a little further north. If you want to be the only boat in the bay...it probably won't happen.
BUT - it's good you're chartering out of Nanaimo. It puts you smack in the middle of really great options.
North:
As some have said - Princess Louisa is a looong way in. There's no doubt it's spectacular, but since you're paying top dollar to be out there, you want good bang for your buck. It's your call - and it sounds like you have other good reasons to go up there, so it might be a great choice for you.
Lasqueti/Jedediah have been mentioned. I always stop there on my way north to see the wild goats, sheep and hike the trails. Boho Bay is easiest to anchor at, and then just dinghy across to Jedediah. From there you spend a day heading up to Lund, and then by lunchtime the following day you can be in Desolation Sound. In my mind this is equally beautiful to the head of Princess Louisa. As was mentioned you stern tie most of the time in Desolation. Deep anchorages, and lots of people. But the wildlife is cool, the water is warm and the forests are spectacular. After you get your fill in Desolation, you could hop across to the Vancouver Island side again and work your way south - Comox Harbour, Hornby Island, and then finally back to Nanaimo.
If you did hit Princess Louisa, something you might find interesting to try would be to turn south after exiting and stop in Secret Cove or (if you've got the stern-tying nailed - Smugglers Cove) and then the following day blitz it to Vancouver (or go to Gambier Island first). False Creek is where I'd go, and you need a permit to anchor but it's easy to get online. Anchoring off Yaletown and taking the dinghy over to Granville Island to explore the markets and shops is super fun!! Then you are just a 1 day shot back across the Strait of Georgia to Nanaimo.
South:
The Gulf Islands. Again - SOOO many options. The climate is significantly different here than any of the other areas. It's quite dry, and most of the islands are populated, so the shoreline vista is totally different (plus there are far more PUBS!)
To access them from Nanaimo you can either do Dodd Narrows or one of the other passes - Gabriola, Porlier and Active. The ferries all take Active, so it is challenging, and Dodd Narrows is always suuuper busy. Of all the places in the Gulf Islands - that one pisses me off the most. Everyone (including tugs with log booms) waits until slack water and it's just an absolute gong show! Most people will call their entry over the radio, which is great, but many will then pay absolutely no heed to the commercial traffic, to their vessel's wake, or to other vessels already in the narrowest part of the pass. ...but I digress....
Some great spots to see once you get through - Thetis Island (with a lovely honour-system fresh/frozen produce shop and also a pub), Pirates Cove, Montague Harbour, Ganges (holding is not great), Portland Island, Sidney Spit, Bedwell Harbour, Cabbage Island, Winter Cove, the list goes on....and it's hard to go wrong. You would also likely run into the Southern Resident Orca pod at some point.
It was said to watch your anchoring scope. This is absolutely true. Especially in Bedwell. 3:1 is the norm. I mentioned the ferries, and this is something to be aware of no matter where you sail in the southern islands. There are lots of them and they come up fast! Always stay diligent on the helm.
Other than that - try to plan your days using the currents to your advantage (grab a Ports and Passes book) have an AWESOME trip!!!