I have an old database on MSDE which I need to replicate (one-time process) to a new MSSQL 2008 SQLExpress installation. What are my best options to replicate without involving messy sql scripting? I know there are some "layman can use" paid software out there such as dbconvert. I wouldn't want to use them as far as possible but will consider if there are no other alternatives. Thank you.
Doesn't sound like you need replication. Sounds like you need to restore your old database to the new MSSQL 2008 Express instance.
Right-click the database, select All Tasks -> Backup Database. Add a destination file (*.bak) and perform a Complete backup.
In SQL 2008 MS, right-click Databases and select Restore Database. Input a name for a new database and select the backup. After the restore operation is done, the database will be upgraded to SQL2008 automatically.