Build the manual version by hand or spend two weekends automating it first Cut the Scope

Do it by hand until it hurts, and be specific about what hurting means so you know when you have arrived.

Right now 90 minutes a week for six people is completely sustainable. Automating that saves you 90 minutes and costs you two weekends, so it pays back in about ten weeks if nothing breaks, and something will break because you already said the site changes layout.

The number I would use as a trigger is subscribers. At six, do it by hand. At fifty, the manual version starts costing real time and the digest matters enough to be worth building. Between those, automate the single most annoying step rather than the whole pipeline. For most people doing this, that is the copying, not the sending.

There is also a thing you get from the manual version that you cannot buy later: you will notice which listings are actually interesting, and that judgement is the only part of your digest that a scraper cannot reproduce.

Split the difference. Do not build the scraper, build the boring middle. A spreadsheet with the columns you fill in and a template that turns rows into a formatted email is maybe two hours of work and cuts your 90 minutes to perhaps 50. Scraping a site that changes layout is the expensive fragile part, and the formatting and sending is the cheap durable part.

Automate durable things first, fragile things last, ideally never.

Track where the 90 minutes actually goes for two weeks before you build anything. Everybody assumes it is evenly spread and it never is. Mine turned out to be 60 minutes of searching and reading and 30 of everything else, which meant the pipeline I was about to build would have saved me half an hour.

Six subscribers who are all people you know is also worth thinking about. Before spending two weekends, send it to twenty strangers and see whether anyone opens it twice. That tells you whether the automation is worth building at all.

One risk of automating first that people underrate: once the machine is producing it, you stop reading it closely, quality drifts, and you do not notice until someone unsubscribes. The manual version keeps you honest for as long as you can stand it.