I would recommend running a 70V line to speakers with volume controls to locations near where you want them heard. Then you can have a paging microphone and everything in one clean location.
I like Bogan as they used to last forever eg Bogen C35 Public Address Amplifier - IP Phone Warehouse
Speaking of cables, what does one really need for a 40' run? I know some guys insist on 2 gauge micro-braided solid gold, but what is really reasonable?
OP bought powered speakers, so should be balanced signal wire not speaker wire. XLR or TRS. Headphone jack is unbalanced which can adpapt up to 1/4 TR. Over 20 feet you want balanced.
You never went roller skating ?
Well, roller blading...although at a roller rink. Most of the sessions played dance music...this was in the early 90s, I was in my early teens. They did have an organ skate on like Wednesday night, and a few of us went once. We never went to that again lol.
I just went roller skating for my 37th birthday. Had a BLAST! The kids loved it. We might go again this weekend.