1. REPORTS.DIC does not work consistently on a VM shared folder! Make sure your sysadmin creates a windows share on a readily available server other than your gp sql server. We have an "admin" server where I keep our SmartConnect UI with related services and this is where we have a share for the REPORTS.DIC. Took a week to figure that one out since I realized the first shared folders were not created in windows... Reports printed in the test environment but once we moved to production GP would sometimes lock on the user or in one case run for 30 minutes and finally return a generic SQL error. The worst part was that as heavy SOP users, our order transfer functionality would hang because it was trying to print the transfer report but of course we thought it was a workstation issue.
2. The GP upgrade proper ran quite nicely and even picked up an addon I missed in the first pass. Seems very stable. Of course, this was the easy part; the difficulty lies in the companion products and stored procedures/triggers added. We worked up some scripts to identify the sprocs and reload while applying proper security at the same time.
3. I did everything I could in advance. I upgraded SmartConnect and then for the gp2016 upgrade just had to go into Setup/SmartConnect Setup and switch the SmartConnect Dynamics GP Connector/GP version to GP2016. It rebuilt all the maps but was very clean with no complaints.
4. I had our security admin create me a list of all workstations with GP and then used that as a checklist for the client installation.