I know adding or modifying massive areas would be a huge pain in the (blep)!
**as a note I am not a programmer.game developer**
So here is my idea, the world of elder scrolls is a high magic world, why not sell stones that "gate" you to a housing instance/guild hall. They could be somewhat generic interiors size dependent on which stone you buy. Perhaps the portal has a timer so anyone in your group can journey with you if they are where you open the gate/portal and use it within say 30 seconds.
Just a suggestion to easier implementation with satisfying the community as far as places to meet up