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Java is a huge plus over Python for me, namely type checking and ease of deployment.

I don't know either jailer or condenser, but I know that jailer@java has an unreasonable better change to have less bugs then condenser@python. Like you already noticed, condenser produces errors during run time.

I just took a quick look at condenser application you linked. Only supports Postgresql and MySQL. This is often the case with none Java tools. They tend to support a select few number of databases. With tools that support JDBC you will be able to connect to most databases. That is often my challenge as someone who works in BI.

May I ask why you decided to use a condenser?