Actually you can short circuit the procedure some what - update to 3.3.7 or so - take a site template of the updated site. Off line install a brand new v4.9.3 or v5.0.1 fill these out with any modules that you require. Then use the wizzard to import the template created under V3 - this will work 80% of the time - so far worked for all my clients ( will not work on v5.0.0 ) if you import the event module this may cause some problems but every thing else appears to work ok even 3rd party modules .

This will not however import your users - to do this check out the module from www.phdobson.com  (BulkUser Manager) this will move your users and roles from V3 to V4 and it is a low cost module that is ideal in managing users where you have a large number of users.

If the site import works for you then export a site template, setup a brand new DNN online and install the required modules then simply use the site wizzard to fill out the database.

Much faster then going thro the updates in V4. and you can do the lot offline - may not work for all configurations of dnn but it is worth a try offline and only takes a short time to try on your configuration. If you go to V5 and you use UDT then the wizzard will not import your content for this module as the module names have changed it appears.

I found problems going up the V4 updates - some worked ok some did not so you had to recover and start again time wise the above was the fastest solution.