Help with moving from My Movies to Kodi

My current setup is:
– My Movies/Clients running on 2 HTPCs, 2 iPads, 2 iPhones
– Windows 10/Windows Media Center (WMC) Hack running on both HTPCs
– My Movies/Server running on Windows Home Server (WHS) 2011 (1,500+ movies & TV series in Video_TS & .MP4 formats – yes, I decided to support both options).

Since WMC and WHS 2011 are no longer strategic/supported solutions, I’m trying to put plans together to sunset these technologies and move to Kodi as my Media Center Platform and Windows 10 for my home server.

Note: I set this system up for my handicapped son so he could easily manage accessing and launching his movies & TV series from his iPad. Since then, the whole family loves this system. I’m sure moving to Kodi will be a significant improvement.

Does anyone in this forum have any experience/learning’s they would be willing to share with me to help me plan out these moves?

Any and all assistance would be greatly appreciated. Thank you.