1 – it’s a question that only you are qualified to answer. If you want to automate your process and have the necessary cash (=$$) as well as the time to devote to learning, it seems to be a worthwhile investment. While you are engaged in anything more productive, the machine may batch outboards for you.
2 – I’d suggest that this is a question of personal taste. Easel or Carbide Create will get you up and running with the least amount of trouble for absolute ease of usage. It is inevitable that you will outgrow their talents over time. However, you do not need to be familiar with climb vs conventional milling, step over, or a slew of other technical terms in order to get started. For the most part, any hobbyist-grade equipment will be compatible with the default settings.