Okay, so you got me price-shopping again, because I seriously would buy an annual policy in a heartbeat. But my needs must be different from yours.

Here's what I found:

Travelex is cheaper and has more "options" (https://www.travelexinsurance.com/tr...nsurance/plans, scroll down to see ultimate vs advantage vs essential, etc.), but the trip delay coverage is capped at $250/day.

That does not work for me. $500 per day is the minimum coverage I need for three reasons: (1) even in weather situations, I've had decent luck getting AA and DL to cover $100-200 in expenses, (2) the hassle of sending in the paperwork really only becomes worth it at the $400-500 range, and (3) my typical hotel/uber/food bill is in the $400-500 range on these overnights anyhow. I really just want a policy that covers some food and my reasonably upmarket hotel (not Ritz, but not dumpy Sheraton either -- typically the most convenient in-airport hotels for "stranded" situations, like the GH DFW, the Westin DEN, etc., are in the $300-400 range).

Next I looked at Allianz, which had a midrange policy with a $600 delay coverage and a premium policy with $1600 per delay, but nothing on the website before you buy indicates the daily limit. (The marketing PDF indicated that "your declarations" will govern -- but of course no decs page was available until after purchase.) The Allianz policies were more expensive ($280 for the midrange policy and $510/yr for the premium policy), but I went ahead and bought the premium policy for $510 to see what it offered. No declarations page was made available online even after I purchased, so I called, and an agent emailed me a PDF with the declarations page, which stated that the travel delay coverage was actually only $200/day, for up to $1600 total. A farce. (I suspected the daily limit was less than $1600, but I held out hope that it was $400+). I called back and endured a 10-minute cancellation process to get a refund. Also, note that Allianz has a 6-hour minimum on the delay, so the coverage isn't that good anyhow (though it does not have the Citi AA restriction; any aggregate 6-hour delay is fine).

Finally, I checked TravelGuard, sold by AIG (which administers Amex Platinum's trip delay coverage, which offers $500 for a single-day claim), but it too has a $200/day max on trip delay coverage.

It does not seem that, at any price, the kind of policy I would like is available on the market.

I would love for someone to direct me to an actual policy that offers the coverage I seek. (People on this forum love to say "haha you should have bought trip insurance" -- but in my experience, there is not a lot of good coverage, probably because the frequency of substantial delays is just too high.)