Realized I didn't answer your first question, tl;dr Jobber is... fine. It's not great, and the support staff doesn't seem to have any mechanism to actually improve the product, but it's still good enough that I pay for it and continue using it. For context, I'm running 4-5 calls/day, and the appliance shop that I work with handles scheduling and data entry into Jobber
I created a spreadsheet with gripes about Jobber. I haven't shared it with them, because everytime I reach out to chat or support the agents seem to find a way of telling me that the bug I'm reporting is actually a feature, seem to have zero urgency in actually fixing it.
One example, if you want to send a customer notes from your visit on letterhead (to male it look 'official' as opposed to sending a typed email), but not charge any money for the visit (say it's a callback or wty call), the only way I've found to do that is to create and send a $0 "invoice", but jobber still treats that $0 invoice as a receivable, and sends a payment reminder to the customer after 30 days unless you opt to collect a '$0 cash payment.' That's clearly a bug, but jobber support told me that it was a feature because of how committed jobber is to making sure we get payed ($0 in this case)
Here's a link to the spreadsheet of jobber bugs I've been tracking (loosely)
https://docs.google.com/spreadsheets/d/1VSvHDwHIHf1Horz7zFh7TGUdrktI2jr2gVm1zuPSwPg/edit?usp=sharing