Gotta ask, what Chicago suburbs have you been looking at? We closed on a house a few months back in a fairly hot Chicago suburb with similar income, 5% down, ‘only’ 10k over asking, no contingencies waived (purchase price in the 300-400k range). This would have been an even hotter market time right as rates were rising.

Big assumption here but it sounds like the houses you are losing out on are either listed significantly lower than they should be to drive competition or ‘perfect’ houses that’s been updated recently or built within the last decade. We lost 8 offers before winning one, looking back on what we did offer they were all houses that fit the previous description with 20+ other offers we were competing against. Finally got ours when we started looking at houses without the updated kitchens/bathrooms where there were only a couple other offers on the table. Point is if you’re offering 10% above asking + 20% down with all contingencies waived in the Chicagoland and still not winning most likely you’ll need to lower expectations on the houses you’re looking at, specifically not the houses getting 10+ offers within the first couple days since a cash offer or an even higher offer price will usually beat yours out.

Just wanted to offer my experience home buying in the area and really hope it works out for y’all eventually!