If it were me, I would want to totally rebuild the database. I think you could make things easier if there were more fields like if you select that it is a movie pin, you would input specifically what movie. A place where you could list what characters are on the pin. A place to list if its part of a series and which series it is from. This would eliminate the need for so many pin groups, and they wouldn't need updating since everything could then be searchable. Also, a field for the backstamp wording. More picture slots. Not to mention, all the other improvements people say they want like the ability to prioritize wants.
In that case, I think it might be easier to create a brand new database, input the existing information, with all the new additions. Since they appear to be hiring out the backend work, I wouldn't expect to see much improvements to the existing database because that would completely go away and would just result in unnecessary "busy work." When the entire new database was ready for prime time, then switch it over all at once.
To use as an example. I have a bunch of pin frames to hang in our spare bedroom. I could just hang them, show I accomplished something. BUT, I want to paint the room. So instead of wasting time hanging them, I am waiting until after the "back end" in this case, a paint job is complete. So its one big change all at once, instead of doing something minor, then doing the major change later.