So those are a lot of obstacles to overcome, but I can honestly say I don't HATE their room anymore. And to make matters more awesome, they keep it pretty clean now. It took some major rearranging, and, of course also involved a playroom remake. So here are some befores, afters, and tricks I used to make the playroom and my boy's room places I don't absolutely abhor, and instead places that are nice, inviting, and will hopefully make someone else desperately want to buy my house down the road :)
I decided their closet, which was such a mess of shoes they rarely wear, needed a makeover too. I needed a place to store football stuff too, since they are playing year round now, we always have equipment, plus they need access to compression tops, shorts, tshirt, jerseys, and pads so I'm not having to locate them 5 minutes before it's time to leave. So I emptied the bookshelf and stuck it in there. Now all the shoes they rarely wear are in there, along with a shelf per boy for football stuff. Then the shoes they wear often have a place in the front, but it is only one pair per boy.

Shelves I made for under $30, my fav being the top shelf with their football pics and trophies. Thanks to friends who caught these awesome photos last season. And a third wall with more football awards and pics. My mom bought them those football player collages. I love them since filling them with cute pics from last season....that, again, I got from friends.
And the bed covering the window. I still don't love that situation, but it's what I have to work with, so....yeah.
The walls still need some work, so if you cute stuff you want to get rid of, message me, I'll send you my address. :)