Match Data, Insert data when matched, do again with different criteria

I would appreciate any assistance that anyone can give me. I looked at previous threads and tried to use some of the code posted for similar issues, but am utterly clueless with VBA, especially in Excel, so nothing worked...

I have a macro enabled workbook (received from another agency) that I will need to insert 500-700 entries. So:
1) I need to match column B on Workbook1 (Fleet Reduction, Sheet3) to Column F on Workbook2 (VAM, Worksheet 3),
2) There should not be any that do not match, but when they match, I need to take Column F of WB1 (Same sheet) and insert it into Column F of Workbook2.
3) After the VIN information for the detail is inserted to Workbook2, then I need to match only the "red" cells that have a "swap" (workbook2) by VIN number and insert them into Workbook1, worksheet2, Column R. Once it has been inserted in Column R (and this is the very coded sheet), Column S needs to be changed to submit.

I currently am able to attach the Workbook 2, but workbook 1 is too large, even when I have removed the code, most of the data, and all macros. I can e-mail it, or if anyone has any suggestions as to how to reduce the size, I would appreciate it...

There will be a total of 13427 matches/data inserts the first round. There will be 500 to 700 the second round of matching and inserting.