a Don't feel stupid, took me quite a while to get the hang of DCG at first, we all have to start somewhere.
b No, it was built in Win7.
Just loaded it up again, enabled as 3rd party campaign in DCG, went into IL2, started a new campaign, began at the beginning, and it generated the campaign without problems... so I have to assume that if the campaign shows up in IL2 then the files should have been transferred correctly in jsgme, particularly if everything else shows up too, leaving only the third party campaign set up in DCG as questionable. The error you're getting is saying the campaign files aren't there, which normally means it hasn't been enabled as 3rd party in DCG so DCG is looking for campaign files it hasn't created yet, hence the error message.
Check again that it really is enabled as 3rd party in DCG, you should get a window asking to navigate to the campaign directory (Missions/!DCG Clash of Eagles BoB 1940) and once you open this directory you should see an allcampaigns.dcg file, alone, nothing else. Double click on it or click OK, same thing, and the campaign is enabled in DCG. Then close DCG, open IL2, go to campaigns, select CoE etc, and it should then work, unless something is drastically wrong like you have DGEN active not DCG, only have one of the 2 downloads, or a download is corrupted, something is screwed up in jsgme, or you have gremlins.
Just to be sure, open DCG, open the Files menu, and there should be an entry "Optional Third Party Data Folder". If this isn't ticked then the campaign isn't enabled. If it is untick it, and go through the procedure again to make sure it's the right campaign and you don't have some other campaign enabled. Check under Mode for Off-Line Career (Full Auto Generation) and Replace Career generator (DGEN), both should be ticked.
Look in the DGEN folder for a confgb.ini file (or de), open this and see whether it points to the CoE campaign (BoB7), and the actual generated campaign files.
Pilot,RAF,York,1912
gb01
dir=missions\campaign\gb\DGen_!_BoB7pilot0 <----------- this is where your campaign files should be
Language=Russian
instant=false
BoB7 HurricaneMkIb
BoB8a HurricaneMkIb
BoB8b HurricaneMkIb
BoB9 HurricaneMkIb
BoB10 HurricaneMkIb
Go to this directory and look inside, should be a load of files. If there are only a few then the campaign isn't generating correctly for some reason (usually an error in the campaign, but we already know it works). If there is a squadrons.dcg file in there, you may have to reset the active campaign in DCG, can happen. Open DCG again, click on the little folder icon, opens another window asking for the squadrons.dcg file, point it in the right direction as above and again double click on the squadrons.dcg file, this will tell DCG to use this as the active campaign if it got lost somehow.
Otherwise, well, apart from from coming over there and looking at your screen it's hard to say, but everything points to it not being enabled as 3rd party in DCG...
Still, I'll update the files and put it all into an exe file and reupload, (hang on a bit) but you'll still have to set up DCG yourself of course.