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EDIT: Also, I just had him send me his EXE file, in case you meant to literally use the same EXE. Nothing changed.
EDIT: Have you both tried to verify game files through steam?
EDIT2: As a last resort, you could try using BitTorrent Sync to make sure you have EXACTLY the same files on both of your computers. Make sure to NOT make the folder read only when you send the invitation to your friend.
If at all possable i would suggest playing over WAN/LAN.
Also there are Fan made random map generators, these seem to have less bugs and more customazation. You may wanna check maps4heroes and download a few premade maps.
Just to let you know, in the 'maps' folder found in your HoMM:TotE folder, you and your friend need the SAME maps(ALL of them not just the one your playing)
Honestly it sounds like a map issue, but it could just as easy be a software glitch or even something Ive never seen be4. If you need links cause your unable to search for them, let me know.
Best of luck!
Thread of the MOD -> http://heroescommunity.com/viewthread.php3?TID=41303
Facebook page of the mod so you can ask questions -> https://www.facebook.com/mightandmagicheroes5.5
How to install the mod -> https://www.facebook.com/notes/might-magic-heroes-55/installation-guide/760314834079382