I recently upgraded and had to run some sql queries to get nGen fields compatible with EE2.
Bit of a painful process, but worked ok in the end. See this thread for some help.
Should also mention that for a lot of legacy field types I simply changed them to ‘text’ fields before the upgrade and then changed them to EE2 versions/alternatives afterwards.
It was a 3 site MSM build with thousands of entries which used gypsy also, I ended up having to merge all the fields via sql, into 1 big field group for each site and then use publish layouts to recreate the functionality.
Biggest problem I had was with the scaling problems of the EE2 filemanager. If your site has thousands of files in the directories, good luck making it usable for your client.
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