It's really tough, I'd actually assume you'd have the same problem with The High Ground as it's essentially the same scenario with different deployment.
The main issue with these two scenarios for small armies (I was in the same boat with my all hero force) is that you can be fairly confident of breaking the enemy first (reducing them to 14 models in your example) but then you're utterly dependent on the game not ending for several turns to have any chance of winning.
I really don't like any game that ends randomly as it skews the odds quite considerably towards one force. This happens a lot in some of the Journeybook scenarios. As memory serves, the Warg Attack one in the Fellowship book can end on a random roll from turn 10 onwards. If it ends on turn 10 the wargs don't have a chance, if it ends on turn 20 the odds tip considerably towards the Wargs, the game should be 'ends on turn 15' or something, whichever turn has been play-tested to be the fairest for both sides. It's the same for the Points Match scenarios, the ending at 25% ruling is far fairer and balanced, I would be quite happy to play all 6 scenarios like that.
However, them's just my feelings, as for how you can win, I really don't know, I actually had a lot of success at this scenario at 1000 points with a mixed Rohan infantry and cavalry list. I used heroic march to get to the object first and form my cavalry in a ring around the objective about 7 inches away. The large base size of these models blocked the enemies advance whilst my 24 Helmingas strolled in and sat on the objective, over the course of the game most of my cavalry were killed but they often blocked the enemy and did enough damage to mean that the surviving Helminga numbers often carried the game. These tactics could obviously be scaled down for 500 points. I know that doesn't suit your all cav army but I still think it would be a good idea to rush the objective first and form a defensive ring (which you're bound to be able to do with your large movement), that way, when you lose fights you're pushed closer to the objective rather than further away. Sure you lost your manoeuvrability but you're still as likely as the enemy to get the charge (50/50 Priority/Heroic Move roll-off) and your large base size will make it incredibly difficult for the enemy to get models onto the objective (or to swarm/trap you for that matter). In that way you actually turn your problem into your advantage. Put yourself on the objective, get broken and
you'll win if the dreaded 1 or 2 comes up.
If you don't like that idea, the other key thing I've found when you're playing Hold Ground against a numerically superior army is to come as close to breaking the enemy as possible
without breaking them in one turn. So, say you begin turn 6, 4 models from breaking the enemy, I would do everything in my power to only kill 3 (if you're charging don't throw spears, bash where possible, shield where possible) so that the turn ends with the enemy's army one model away from breaking. In turn 7 go all out and try and kill as many as you can in the one turn. The enemy will be broken at the start of turn 8 and then you get another full turn of combat before the game could end. What you don't want (in the example above) is to kill 4 models in turn 6 as you then only get one more turn of fighting to reduce their numbers before the game could end. Don't get me wrong it's tricky to pull off but it makes a huge difference.
Obviously, once they're broken, you should do everything in your power to charge their captains so there's no stand-fasts and they all leg it.
Finally, the most important pice of advice - don't roll a 1 or a 2
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