1) Ascalon's war against the Charr is not going well. If defeated Ascalonians will have nowhere to run.
2) Deldrimor Dwarfs have turned into Stone Dwarfs, and went underground to chase the Destroyers. So most of the Dwarf towns are currently ghost towns.
3) Stone Summit are mostly defeated and will provide minimal resistance.
4) Charrs some what do not like cold weather. They will be hesitant to chase the Ascalonians across the snowy mountains.
5) Kryta is locked in a civil war and will not be able to effect this take over.
6) The Dwarfs left behind many strong fortifications that Ascalonians can use against the Charr.
7) Shiverpeak's mountainous terrain is easier to defend than the open fields of the current Ascalon area.
I propose that Ascalon take over the abandoned Dwarf towns in Southern Shiverpeaks. This way if Ascalon is ever defeated by the Charr at least the people will have somewhere to run. Else the Ascalon civilians might face a slaughter.
Now is the best time to do this take over, since the resistance in Shiverpeaks will be at its lowest in the last few centuries. The Stone Summits are mostly defeated. Kryta is at a civil war so they can't stop us.
We can lead the people from Yak's Bend to Beacon's Porch. From there down to Deldrimor War Camp. From here we will split into two groups. One group moves south to take over Droknar's Forge. The other group heads east to take over Thunderhead Keep. Along the way soldiers will protect the people from wild life and Stone Summit attacks. We Ascalonian warriors have fight the Charr for ages. A few Trolls and Stone Summit escapees don't have a chance against us.
If successful, we would have ensured the safety of Ascalonian civilians. The Charrs do not really like cold weather. If they try to attack us in Shiverpeaks their fighting abilities will be weakened. And the Dwarfs had left behind many strong fortifications for us to use.
We Ascalonians are brave and will gladly defend our homeland with our lives. But at the same time we should have a back up plan for the Ascalon civilians in the worst case scenarios.