It seems odd that Strong Bad bets the shades of Homestar's Dangeresque counterpart rather than his, until you remember his huge record for stealing things. Not to mention why would be bet his prized sunglasses?
You can win the Pac Man watch off of Tycho. It's no wonder we haven't seen it in the comic for awhile.
The watch normally finds its new owner through the murder of the previous owner. The Team Fortress 2 characters respawn whenever they are killed, with their current loadout. That's why the Spy still has it.
Max seems to be extremely lucky when it comes to getting that one card you need on the last river card. More so than the other 3 characters. Then you remember his latent psychic powers.
If you leave mid-tournament, and restart the tournament from where you left off, the eliminated players won't be performing their respective Funny Background Events - they'll have left. It makes sense that they didn't want to wait for you to return.
Max's collateral is the Lugermorph and the License to Maim, but the License to Maim has a 1 on it, meaning it's actually Sam's. At least that explains why he doesn't seem to mind losing it.
The same goes with Strong Bad's Dangereque glasses; they actually belong to Homestar Runner.
Why is Heavy a conservative player that only moves in when he's sure? That's exactly how a good heavy in TF2 should play, going in too early or not being sure would mean falling prey to spies or snipers, his low speed also means that he has to pick the right way to go every time, or stay back and think it through.
The Heavy apparantly has a fear of ghosts. This makes sense given that in his own game, there was a Halloween event featuring a ghost whose purpose was to immobilize players with fear. That, and the following year's Halloween event centered around a headless ax-wielding revenant.
Heavy thinks Huey Lewis is new, while Tycho is a little baffled at this notion. Heavy's been updated to modern times, but Russia (or at least, the area of Russia he lives in) is itself a few decades behind the times (which really happens in some out-of-the-way places).
Heavy calls the Iron Curtain "Sasha". He's also willing to give it away just to play poker. It also functions identically to the normal minigun. Maybe he lost Sascha in some way, and he made another gun to replace it, naming it "Sasha" without a C? Maybe Sascha broke and Heavy made the Iron Curtain out of the metal that was left?
When the Heavy bets in using the Iron Curtain, he says that all his money went to buying "gifts" for Sasha, because she's been "very good". Maybe it is the original Sasha, just decked out with 10,000 dollars worth of decorations and whatnot.
Why is Heavy willing to part with Sasha? It's not sasha. He clearly pulls a un-modified Sasha on Tycho in one if his Eliminations, the calling the Iron Curtain "Sasha" was simply an extended con on his part (Although it's clear he's fond of the Minigun). He probably won it himself at an earlier game against someone else or otherwise just got it.
The Heavy tells a story he finds hilarious about tearing an Engineer's fingers off and jamming a wrench down his throat and watching him scream for his mother. Meet the Pyro reveals Pyro is the only (wo)man he is afraid of. What, exactly, this says about the things the Pyro gets up to in his/her spare time...