replied on January 9, 2020
This should go very easy. If you are on Laserfiche 8+, I always recommend just waiting to upgrade until on the new OS since Laserfiche handles upgrading the repository and SQL schema very seamlessly. It should be very simple to just move the database over, install the new software then register it all. The first time you mount the database, it will upgrade it for you.
One thing I would recommend is standing up weblink first and pointing it at the old server so you can get the front end figured out ahead of time as this is likely the only thing that will not be completely seamless. The custom searches and front ends may need to be rebuilt.