If the listings are priced artificially low (Which is most definitely happening here if you are looking outside of the city and losing) then you're going to need to cover that whole spread. When I am reviewing contracts with my sellers an offer 50k over doesn't mean shit if the buyer can't make up the difference should an appraisal come in low.

It's often more advantageous to go with a lower offer that will cover the whole thing if that number comes in just a bit above comparable properties. You really don't want a seller going wild for the higher offer only to have the appraisal come in low and the seller making out with less money than they would have.

I'm guessing it's a combination of both things here. Artificially low price and not adequately covering the gap.

edit: I should expand on something that gets missed often. When listing agents list low they're doing two things: One making themselves look like fucking heroes because they got "over list", and two they're baiting out people who do have the cash to put into the deal and weed out people who will rely more on financing. This doesn't mean you or anyone else are losing to all cash buyers, just people who can put more skin in the game. Both of these things are incredibly common and dumb and really only serve the listing agent on the deal and not necessarily buyers or sellers.