
Karl and I got together recently to try out some big battles in Song of Blades & Heroes, our go-to skirmish game (and the ruleset that helped this game club coalesce in the fall of 2010!).
Though it has a well-designed rules engine, Song of Blades & Heroes is definitely meant to be played around the 300-point benchmark, which equates to anywhere from 5 to 10 models per side. Seeing as how our club has dozens of SBH games under its collective belt, Karl and I decided to push the envelope a little bit and try out a 500-point game, followed by a 1,000-point game.
Playing at this level required two important rule tweaks: We required 1 leader for every 250 points on the table, and we allowed each player to fail one additional quality roll before his turn ended. Normally in SBH, if a player rolls two or more failures when trying to activate a figure, his turn ends immediately, even if he hasn't activated all the guys on his side. With this change, it gives the player one last chance to get something going, even after he fails once.
Both of these changes enhanced the game immensely and really made things hum at the 1,000-point threshold.
In the first game, Karl's 500-point elven warband faced off against my 500-point dwarven squad. In fantasy, the elf/dwarf animosity is a known quantity, so it was a cinch to come up with a plausible scenario: the two warbands were trying to take control of a small hamlet located on the windswept frontier. Whoever controlled 2 of the 3 buildings on the table by turn 6 would be the winner.
As it was, the 500-point game was hardly a contest. Karl's force was much more optimized than mine ("That's very 40k of you," I recall saying as he carefully positioned his troops to box out my dwarf leader), and he won a clean victory by slaughtering my poor dwarves and occupying 2 buildings.

In the second game, Karl recruited another warband, this one composed of fanciful woodland critters, alongside his elves. I added another 500-point hobgoblin warband as allies for my dwarves. We set up another scenario using a big ol' 3-tier hill in the center of the board. The objective was to seize the high ground and hold it until the end of the game. The side with the most troops atop the hill would be the winner.
Then we added a fun little wrinkle: a "fast travel" rule that allowed models to enter a passage behind a waterfall and emerge, one turn later, from a cave at the base of the hill objective. Here's the layout:

We actually used this rule quite a bit, and it resulted in some fun photos, such as this dwarf warrior emerging from the caverns to aid his fellows atop the hill. That is SO METAL!

At 1,000 points, we found that our turns took a bit longer than a typical game, but the house rule allowing two "fail out" rolls meant that we were still able to mobilize our dudes. Karl sent his elves charging to the top of the hill, where they met my huge troll warchief and his big honkin' axe. He was full to the brim with special rules (that's very 40k of me) and he held the elves at bay for several turns before dying.
Across the table, a major fight was developing around the waterfall. My dwarves attempted to create a stout blue line to block the entrance to the cave passageway, thus denying Karl the chance to use it to transport his guys across the table. We quickly added another house rule about the waterfall: it was actually holy water, and models standing in it received a bonus to combat! Here's how that scrum looked.

Yes, that's an anthropomorphic enchidna with a sword fighting against my dwarf crossbowman.
(Side note: It's a lot of fun playing with gamers who aren't super competitive and "in it to win it." The fact that Karl and I were able to come up with flavorful house rules on the fly, all in the name of adding some coolness to our game, speaks to the sort of game environment we've tried to foster with Chicago Skirmish Wargames. I think this sentiment describes just about everyone who we've ever gamed with at a club event.)
Anyway, after my troll warchief was killed, the game started going sideways for me. I still pulled off a few upsets, though: I used my flying manticore to swoop in and kill Karl's elf leader, which resulted in a morale check for his guys, and I sent my two mounted knights galloping up the hill to join in the fight the last minute. Here's how the table looked just before my troll warchief bit the dust and we called the game.

On the middle tier of the hill you can see my four hobgoblins swarming up the slope while Karl's two pesky critters (a hyena and a cougar) harried my flank. Atop the hill, my troll warchief is doing his thing against a gaggle of elves, most of whom are wisely keeping their distance.
All in all it was a fun game, and we proved that larger SBH battles are not outside the realm of possibility, at least for experienced players.
— Patrick, Chicago Skirmish Wargames club member