Please check out these incrememntal steps from Mitchel Sellers blog....specifically here:
Incremental Upgrades?
One common question that I get from
people is which version of DNN is safe to come from with a single
upgrade to 4.8.3. In my experiences I have found that if you are on a
version < 4.4.1 that it is best to first upgrade to 4.4.1, then to
4.6.2, then to the most current version. I know people that have had
success with direct upgrades, but I have found them to be more
successful following this pattern. If you are currently on a version
between 4.4.1 and less than 4.6.0 I would recommend going to 4.6.2
first, then going to 4.8.2.
The main reason for this
recommendation is due to the major changes in 4.4.1 regarding site
performance and in the 4.6.x version and the authentication provider
system.
To see the entire blog, visit this URL:
http://www.mitchelsellers.com/blogs...om-4x.aspxHope that helps!