7 years for a response to a very relevant and important question; this post seem to have got lost in the laracasts database. I'm not much help but here's my two cents...
After many years with Laravel I still struggle deciding between two approaches: Cashier (stripe subscriptions) vs custom recurring charges.
I know Stripe Subscriptions and Cashier do a lot of the hard work for you but custom eloquent models have fewer limitations than the Stripe subscription model, and add to that Laravel queues, jobs, events and scheduled tasks; the Stripe PaymentIntents API combined with core Laravel features seems to cover everything that Stripe subscriptions provide, but with more flexibility.
Still I'm never sure which way to go and I pull my hair out for weeks before making a decision on each project. Currently I'm building one project with cashier and one with custom recurring charges. On the cashier project it's been quite difficult to handle bespoke features such as non auto-renewing subscriptions and gift subscriptions (museum membership). On the custom project I'm not confident that charges will keep working in the far future.
I'm more comfortable with the custom flow but the development community always pushes me towards Cashier and subscriptions. Maybe I'll realise why someday....
My current conclusion is that both approaches are valid and workable for most projects, but maybe, just maybe, I should avoid cashier and the stripe subscription model. I feel like any successful project will someday want to break out of the constraints that those models impose. Stripe subscriptions seem like a poor substitute for custom laravel stuff, but that implies that Cashier is an inferior approach. Take my words with a grain of salt because Taylor and Jeffrey have put a lot of work into cashier and the community consensus is to use cashier and stripe subscriptions.