You sound like you've got a pretty full schedule already.

If time gets crunched, you could go to the high-altitude zipline at Rio instead of the Skyjump at Stratosphere, as Penn & Teller perform at Rio. (I once had a girlfriend who wanted to do the skyjump, and we joked that I would be happy to push her off a tall building. In the end, I would have been extremely happy to do so, bungee cord or not!)

If you and your friend are good-looking, you should be able to get into a nightclub or a beach club for free. But I don't know precisely how that stuff works. My ex used to work the strip, basically trying to get hot girls or free-spending men to go to clubs, from which she got a commission. I guess you could look on Craigslist to see if some of the promoters advertise there.

Delano is nice, I stayed there about 12 years ago. $300/night (all in, including taxes and resort fee) on a weekend with the Amex FHR amenities isn't a bad price. Pretty much every hotel in Vegas has a resort fee so just think of it as built into the price.

I wouldn't say you're too late to do anything Friday night, although I think the nightclubs do close at 2. But do pay attention to the jet lag. If you're like most people you'll be up early on Saturday and falling asleep early Saturday night.

You should be able to get discount tickets for P&T. However, do check out the prices. They have a few ticket kiosks like Tix4Tonight but they're not necessarily good deals.

Have you seen Cirque de Solei? I think of that as being much more iconic Vegas than P&T. I don't think there's that much difference in the quality of the shows vs. price, so you could easily go to one of the cheaper shows at Aria or Treasure Island. I haven't been to the Cirque Michael Jackson show at Mandalay Bay (I think that's where it plays) although I might go on my next trip.

Take Uber or Lyft. They've raised the prices significantly but it's still much cheaper than a taxi.

With regard to gambling, if you don't want to, then don't. But if you want to, I'd suggest:
a) Play the pass line at craps. You can't screw it up and it's one of the best bets in the house. You can play the free odds also, but since you're risk-averse, there's no reason to.
b) Absolutely don't play more than $10. Most of the strip casinos will have a $15 minimum, particularly on weekends. Excalibur might be lower, I don't know. I know Hooters is lower, and that's the only place I can think of offhand that's in your neighborhood. If you do go to Rio, Gold Coast is across the street and very likely will have $5 tables (but don't count on it on a weekend evening).
c) Stay away from roulette which has horrible odds, and slot machines which are worse.
d) Avail yourself of the free drinks, but don't forget to tip the waitress a buck or two. You can tip with chips, although you can't buy anything with chips. (Why? Because a tip is voluntary, whereas paying for something in a restaurant or gift shop is mandatory.)