Can I Trade Between Pokemon Red (Gen I) and Pokemon Crystal (Gen II) Via VBA on my iMac?

Solution 1:

Only certain emulators or other third party software can be used to complete this. This video may be able to help:

The user in the video uses a program called TGB Dual which allows you to effectively run two (compatible) versions of the game (i.e. red and blue, or silver and gold, etc.) on the same "console". From here, you can then carry out the trade.