1. No, personal edition does not include transaction logging or PayPal IPN, but all the other licence options do. Yes, Transaction logging allows you to see revenue information from within your
wp-admin dashboard. You can read more about
PayPal IPN here.
2. The current version of JobRoller does not include different types of registration (employers vs job seekers), however this is a popular feature request and likely something we may see in a future release of JobRoller. I can't confirm when this might happen though.
3. There isn't a built in feature for ClassiPress to manage this aspect. You can obviously prune ads, but this only takes the ad itself out of published status. If you have your option to relist ads on, then obviously your customers can relist their ads after they expire.. so if you have gone and deleted the images, it will cause issues, hence ultimately it would be a manual process to remove them.