- Probably a good plan
- Indexing is definitely favourable in circumstances where you want to have access to the documents outside of DTPO. For example, if you want to have them available via dropbox on computers without DTPO, or from Dropbox’s web interface, or from a mobile device you do not have DEVONthink To Go installed.
I have a few apprehensions about your proposed setup though. As I understand it you have (at least) 2 Macs with DTPO. It sounds like you aren’t using the sync feature in DTPO, so my mental model of your setup is this (Note that Folders are called “Groups” in DTPO, but I’ll use Folder here for the sake of being generic):
Mac A
Database A
Folder A [indexed, stored in Dropbox]
Folder B [indexed, stored in Dropbox]
...
Folder X [indexed, stored in Dropbox]
Mac B
Database B
Folder A [indexed, stored in Dropbox]
Folder B [indexed, stored in Dropbox]
...
Folder X [indexed, stored in Dropbox]
Mac A and Mac B are independent and the DTPO databases do not communicate with each other.
In theory, files added/removed/changed in the folders that correspond to Folder A (or B…X) will sync across dropbox and when the Database updates indexed files, the modifications/additions/removals will be reflected in DTPO.
Where I think you might run into difficult is if you add a new folder to Dropbox that is not in an already-indexed folder, lets say it’s Folder Z, it won’t appear in DTPO. You’ll have to instruct DTPO to index that newly-created folder on both Mac A and Mac B.
Similar situation arises if you create a new document in DTPO (rather than creating it directly in the folder in Finder) – unless you say “Move to external folder”, that newly-created file will not show up in the Folder in Finder and won’t sync.
You may also find that some DTPO-specific metadata (e.g., labels, tags, etc) will not survive the sync process (though much of it will, since much of that metadata is industry-standard stuff fully supported by finder).
What I think you might want to try is to use the Sync feature in DTPO and uncheck the “Upload indexed items” setting (which is on by default). This means that rather than two macs with two separate and independent databases that cannot communicate, the database will actually sync between your Macs. Any documents you create inside DTPO will sync across your Macs, metadata for indexed files will sync, and if you create a Folder Z outside of an already-indexed folder, you’ve only got to add it to one database and it will sync across to your other devices.
(see Sync Via Sync Store tutorial)
You’d end up with a database that is synced across devices, which would look like this:
Mac A
Database A [Synced using one of DTPO's sync options]
Folder A [indexed, stored in Dropbox]
Folder B [indexed, stored in Dropbox]
...
Folder X [indexed, stored in Dropbox]
Mac B
Database A [Synced using one of DTPO's sync options]
Folder A [indexed, stored in Dropbox]
Folder B [indexed, stored in Dropbox]
...
Folder X [indexed, stored in Dropbox]
Note that you are working out a single database that is synced between devices (Database A) rather than two independent database on two computers.
If you don’t need access to your dropbox-synced files outside of DTPO, then you can probably just import them to DTPO and use DTPO’s sync to make them accessible on multiple Macs and iOS devices (Using DEVONthink To Go), which is a bit more straightforward than dealing with syncing AND indexed files (I do a mix of both indexing and importing across several databases on 2 macs and 2 iOS devices).
Before you do any of this, make sure you have a good, reliable, backup system in place (other than Dropbox, which is not a backup service), so you are not left with data-loss should something go sideways.