From there, hang around in the bar at the top of the Stratosphere, then catch a show. Since it doesn't seem like bebps can make it, I'm temporarily granting myself his role of corralling everyone to a show. I'm honestly thinking this super sexy Zumanity thing could be fun. After that... explore Old Vegas, and hit some more clubs.
Just FYI, that is a lot of going back and forth. You're going from the north end of the strip (some people consider the Strat off the strip) to NYNY at the south end, then back the other way and more to get to downtown, and then back the other way to go to clubs (not much for clubs in downtown AFAIK - but I'm not a clubbing guy). It doesn't look like much on Google Maps, but it will be slow going (and probably expensive) on a Saturday night, especially with college/pro football starting. I would probably just check out the Fremont Street Experience on Friday when you are going to Oscar's anyway and skip it on Saturday. One night down there is enough for most people visiting unless they are big gamblers looking for tables with lower limits. Also be careful if you walk away from the FSE to go to other places downtown, there are a lot of panhandlers/homeless/scam artists in the area.
This is 100% great advice, don't try and go back downtown Saturday.
If you are trying to people watch at clubs stay on the strip, DTLV honestly doesn't have much on the main drag aside from whatever BS the Golden Nugget is trotting out (it was TROY or something last time in). We checked it out when it was GOLD DIGGERS and they were charging strip prices for a product orders of magnitude shittier. There will be a ton of great clubs near NYNY and Luxor is close.
As for DTLV yeah after Oscars, walk the FSE...there are some cool bars right past Neonopolis near the El Cortez. No reason to go past (or in) Container Park. If drunk don't walk too far from Fremont. If you don't care about seeing MSS/the Cal, just walk directly out from the Plaza. You can see pretty much everything in a night.
Protip: Get a drink at the 4 Queens street bar. Only get a double if a functioning alcoholic.