Sorry for the delayed reply. Just saw this post!!
Question 1...can 2.7 work independently of JEvents now or does it still have to be tied into it?
Version 2.7 no longer requires JEvents at all. It is still available to sync with if you want to though.
Q2...If a user registers using one of our forms in DTR, can they be automatically added to a specific membership in CBSubs, or just to a specific Joomla ACL group?
Using the Joomla auto user creation feature in 2.7 (which is now available per event and can be set as optional or required), the new user will be created as a "Registered" user. There is no tie in to other systems like CB Subs.
Q3...if a user is already a member (registered user) and logged in, do the fields in the form in DTR get pre-populated with info from their profile? If so, which info and can we link info from additional fields in CB to sections in the form in DTR?
Using Community Builder or JomSocial integration... Yes. Now in 2.7, you can sync ANY DT Register field with ANY CB or JS field.
Q4...somewhat like Q3, but opposite scenario. If a user registers using DTR, can fields from the form they fill in be used to pre-populate user profile fields in CB, including additional fields?
Using the auto user creation, when the new user account is created, ANY field that you have setup to sync with CB or JS will be populated with data from DT Register. During the creation of a new user account is the only time DT Register will send data TO the profile.
Q5... as for upgrading from 2.5.x to 2.7.x... is it easy and do we lose data from the previous install?
You would first upgrade to 2.6.9, which is included in the 2.7 package for those that need it. Upgrade instructions are included with it to get you to that point. You will not lose any data here. Of course, you should always backup files and database before making big changes like this. After upgrading to 2.6.9 and seeing that all is well, then follow the upgrade instructions with the 2.7 install files. Again, no data should be lost... except for waiting list records. The waiting list functions like a regular registration process now and just tags the record with a status of "Waiting" so you can move them from Waiting to an active registrant. Any old waiting list records will NOT be migrated into 2.7.
After installing 2.7, go through ever step of the instructions and you should be fine. Also check out the new 2.7 video tutorials to get familiar with everything as 2.5 to 2.7 is a massive jump. Thanks.