Yes, as long as they're both on the same network, and it isn't blocking UDP multicast.
Type it in by hand? Yeah, heh. There are thirty-something waypoints and several elevation changes, along with 8 fuel stops, etc, Since iFly already has it in comma delimited (CSV?) text, I'd like to send that file. If I could find it.
Btw, he does not use iFly, but a competitor EFB. He wants to compare his flight plan through the mountains to mine.
You're asking for a lot--sharing flight plans across different software is pretty hit-and-miss right now. Until the market evolves toward a standard format that is universally supported, a more practical solution would be to use an online tool like skyvector.com to replicate your flight plan and just share the link with him.
Example: https://skyvector.com/?ll=30.74435368...98%20ELP%20KELP
It's not asking a lot if Adventure would tell us where the comma delimited flight plan files are stored.