SoundGuy, I can finally offer some advice in return.
I was an interior Algonquin camper before kids and the move to travel trailers.
Tents are truly a get what you pay for. Believe me I know. Any tent that you can get on sale for $145.00 likely will not last very long.
First you kinda have to decide the style of tent. Is he using it just for sleeping? Then i would suggest a good two person tent. If you need more space, then of course that will not suffice.
I paid $700.00 for my 2 person Moss tent, but that is a rated 4 season tent and could withstand up to 3 feet of snow on top without collapsing.
If you can determine your needs, I can help you hunt down a tent. But I would not recommend anything from CDN tire.
As for fly's....yes, I have used tarps for both a fly and footprint for a tent at some point. It is mostly weather dependant..if the forecast was favourable, I wouldn't even put the fly on. But if the weather is forecasting rain, yes, you would want a fly/tarp and a good footprint on the ground.