For 1), write down the entire manual workflow. Start automating pieces that are easy to automate, even if someone has to run the automation manually. Continue to automate the in-between/manual pieces. For this you can use autonomation to fall back to manual work if complete automation is too difficult/risky.
For 2), look at your system's design. See where the design/tools/implementation/etc limit the ability to easily automate. To replace a given workflow section, you can a) replace some part of your system with a functionally-equivalent but easier to automate solution, or b) embed some new functionality/logic into that section of the system that extends and slightly abstracts the functionality, so that you can later easily replace the old system with a simpler one.
To get extra time/resources to spend on the automation, you can do a cost-benefit analysis. Record the manual processes' impact for a month, and compare this to an automated solution scaled out to 12-36 months (and the cost to automate it). Also include "costs" like time to market for deliverables and quality improvements. Business people really like charts, graphs, and cost saving estimates.