I easily spend hundreds of dollars every year
You might consider purchasing some silk knit underwear, the up front cost is more, but they last a lot longer.
And wash them in the sink (or a bucket) with cold water and some woolite.
Regular detergent (owing to their thin material) is murder on underwear.
Woolite, for all your delicates.
It's elastic. It doesn't shrink, it stretches out and loses it's elasticity.
When I was growing up, there was either boxers or tighty-whiteys. No one complained about their underwear, or even cared what it was. I have 10 year old Hanes and Fruit of the Looms that are still perfectly wearable.
Patrick Warburton's character on Rules of Engagement
said, "When I play softball I wear tighty-whiteys. When I run in boxers it feels like they're shooting dice down there." Or something like that.
It's not the skivvies, it's you. So suck it up, sailor. Being uncomfortable is part of manhood. It's a rite of passage.