ORIGINAL: Korvar
Changing the maps or other major components in any substantive way is an example of what NOT to focus on - that's make-a-wish, Christmas List stuff that makes any updates improbable. You'd have to raise at least tens of thousands of "squiggly L's" (GBP [:D]) to have Slitherine/Matrix seriously consider doing that. The complications are already appearing, and we've barely discussed it.
I believe the focus should be on removing code roadblocks to further 3rd party development. We would be paying for someone to access the source code to which we don't have access, so don't have them work on anything which we can do ourselves. Have them focus on extending access to the internals of the game (not including the 'secret sauce' stuff) so that the community can run with it to create new scenarios, mods, 3rd party tools/utilities, etc. That's how to get the 'most bang for our buck'.
Determining what roadblocks to remove would take a 'Pow-Wow' between community authors/creators and any developer(s) assigned to the project. The community authors/creators could give an idea of what the biggest pain points are for creating a scenario, for instance, and the developer(s) could give an idea of what was technically feasible. Some 'low hanging fruit' could then be determined, and the scope of work set by the quantity of funds we are able to raise.
+1