Recover Bookmarks, Mail, iCal and more after HardDrive upgrade

Solution 1:

Though not a selective copy, you could use Migration Assistant (under /Applications/Utilities) to copy your entire user data from the older hard drive to the Mac. Turn off Time Machine before doing this (to avoid unnecessary backups and slowing down the migration).

Since you already have the user account and Migration Assistant has created a second account, there is no simple way to merge the two accounts (definitely not the configuration used by various applications and the data, since there may be conflicts). But you can copy over data across from the individual folders under the home directory (and somewhat tediously, application data on an application-by-application basis).

See:
How to use Migration Assistant to transfer files from another Mac
Using Migration Assistant on Lion
Combine two+ Users Accounts on the same machine
Transferring files from one User Account to another

Solution 2:

This may be too late to say this but you could have used SuperDuper! or CarbonCopyCloner to move the contents of a case-sensitive backup to a case-insensitive harddrive. (Or alternatively iPartition.) And then have installed Lion which should migrate user preferences as part of the installation process.

Solution 3:

Mail keeps message data in a folder, and mail account settings in a .plist file.
Supposing you know how to access the user's Library folder, you need to:

1. Copy the Mail folder (located in ~/Library/Preferences/) from the old Mac to the new one.

2. Copy the following file from the old Mac to the new one:

   Mountain Lion or newer:

   ~/Library/Containers/com.apple.mail/Data/Library/Preferences/com.apple.mail.plist
   

   Lion:

   ~/Library/Preferences/com.apple.mail.plist
   

The procedure works best if you haven't tried to open Mail before. In case you did, as you try and copy the configuration file or document folder, OS X will ask you if you want to keep the old file, the new one or both.

About calendars (and notes and contacts, and possibly Chrome bookmarks), I'd suggest syncing via iCloud and Google respectively. The offline procedures are comparatively too complicated to be worth the hassle, and since you use Chrome, I suppose you have access to an internet connection. You can boot from the old disk (installed in a HD case compatible with one of your Mac's expansion ports) for syncing.

iPhoto Library is in ~/Pictures/iPhoto Library