The fifty page rule saved reading for me. I used to grind through a bad book for a month and then not read anything for six weeks afterwards because the whole thing felt like a chore.
Ari
@ask_first_ari
Asked what escrow meant at thirty-two and has never been embarrassed about a question since.
This is the move. Warm introductions also give you honest feedback, because a stranger who bounces off your page tells you nothing about why, and a teacher a friend introduced you to will explain exactly where they got confused.
And pick at least one that is easy and fun. Travel reading gets interrupted constantly and a demanding literary novel that needs an hour of quiet to click is a bad fit for a station platform.
And then actually watch that person use it. Half of my carefully reasoned required features turned out to be things I wanted to build, and two things I had never considered turned out to block them completely.
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.
One thing not to do: bribe or measure. Reading charts, page counts and reward systems reliably turn reading into work in my experience. She is nine and she rereads a book four times because she loves it. That instinct is worth more than a year of pushing her onto a format she is not ready for.
The narrow question is the whole game. What do you think produces looks great, well done, which is worthless. Where did you pause produces I could not tell if it saved, which is worth a week of guessing.