Can we talk about booking flights with layovers in weird cities?

I spent like 4 hours yesterday trying to find a cheap flight to Lisbon and kept getting these insane layovers in places like Reykjavik or Casablanca. I finally realized I could save $140 by splitting the ticket into two separate bookings, one to London and then a budget airline from there. The problem is my first flight got delayed and I nearly missed the second one, which would've cost me way more than the savings. Has anyone else tried the split ticket thing and actually had it work out without a nightmare?

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