I've made this run on a number of business trips down through the years.

At that time of night, my guess is that you can make the border from BUF by a little after 11pm, if the flight is on time and you don't have to wait for your bags. BUF is a rather painless airport and the rental cars are in the garage right across from the terminal.

From the border, it should take you about an hour to get to Hamilton. If it were me, and basically all I wanted for the first night is to crash, I'd opt for the Quality Inn in St. Catherines. Its clean, comfortable, and no frills, at exit 47 off the freeway. Numerous breakfast places nearby, including next door.

But for your purposes, I'd check out Niagra on the Lake for the first night. I've never spent the night, but there are numerous lodgings there. Then plenty to see and do while spending a leisurely Friday morning. I'd suspect on a Thursday night off season, there'd be bargains aplenty. Just make sure they know it'll be nearly midnight by the time you arrive.

If you're planning on driving into Toronto on Friday, take into account that rush hour traffic can get pretty nasty regardless of which direction you're travelling. If you want to hang back outside of Toronto on Friday, but move on from where you spend your first night, I'd suggest you check out Burlington or Oakville. Both have very pleasant downtowns.

Burlington has a couple of downtown area Hotels, and if memory serves, these are within walking distance to shops, restaurants, pubs etc. Even if you stay out on the highway, its a 5-10 minute drive to the town center.

The Burlington hotels by the highway include a rather standard Holiday Inn and another Comfort Inn. I typically stay in Oakville at the Fairfield Inn and Suites. Its a newer property and quite comfortable. There's also a Hilton Garden Inn next door. (Winston Churchill exit). Downtown Oakville probably doesn't have as much to see and do as Burlington, but in the other direction from downtown, just across the freeway are several restaurants and a huge theatre complex. There's also a big mall (and more restaurants, etc.) about a mile further up the road.

As for other stuff to see and do in Toronto, if you're at the Hockey Hall, you're walking distance from the Skydome and CN tower. Also within walking distance is the St. Lawrence (farmer's) Market, Queens Quay, and Eaton Centre. And of course, downtown Toronto is absolutely loaded with dining and entertainment options.

I've been going to Toronto at least 2-3 times a year for the last fifteen years, so feel free to pm me if I can help with any suggestions.

Hope this helps. Have a safe/fun trip!