Upgrading a Joomla 1.5 to a new Joomla can be done with SP Upgrade and JMS 1.3 maintenance menu.
We do not recommend using JUpgrade because it can not be executed on the slave sites and when the master is converted into a J2.5 or 3.2, you are not able to make the slave site converted.
With SP upgrade, you can build a second joomla and in fact import the data from a old joomla.
With the JMS Maintenance tool that is still "experimental", you can install a new joomla over a current one and after that have a cleanup of the old one.
In addition, with the "legacy mode" that is experimental, it is possible to make serveral joomla version working on the same DB.
For example have a joomla 1.5 and 2.5 sharing the same DB.
We did that between a Joomla 1.5.26 and J2.5.17
You can not do that with J2.5.18 or higher because the User authentication algorithm has changed between 2.5.17 and 2.5.18 that is not compatible with J1.5.26
We also have successfull created another product to only share the users between 2 different joomla version (again 1.5.26 and 2.5.17) to only share the users.
This is possible with JMS 1.3 and 2 masters sharing the same Joomla definition.
It is expected to present this new "legacy" technology at the Joomla Day Paris between the 23 and 24 may.
joomladay.fr/
The "maintenance menu" also allows verifying the DB structure between the website and and the current joomla or install SQL script.
So when the SP Upgrade can not work on an extension, JMS maintenance may help doing the migration.
Search in this forum because I think that I have already gave some detail on procedure when SP upgrade didn't exists.