Hey @Collin –
With the new releases of Local ( the 5.x line of releases ) this sort of thing should be much easier to accomplish, however there will still be an issue of re-importing the database on the different machines.
If you haven’t done so yet, go ahead and download and install the most recent version of Local from the Releases category her in the Forums:
From there, you should be able to create a new site and store it somewhere like a Dropbox folder. Then, whenever the site is stopped, the database will be exported to sql files within the sql folder for the site.
This will mean that the files and database dump will be syncing, however, you’ll need to re-import the database from the sql files when you change environments.
This is probably the most tricky part if you aren’t using the command line, or some other tool to import the DB since there are so many possible ways of going about this.