Mr. Junkie, from what I understand, the panhandling you describe is SOP aboard flights. I haven't flown Coach since Oct '19 (two flights last year overseas were in Business) and I got "comped" by an Air Wisconsin Captain and Attendant because I found a girl's Driver's License (she was understandably too panicked to look for it), so I really haven't had any first-hand experience observing such.
OK, subject to a COVID CX, when I go to Florida next month, I will carry a reasonable amount of cash. There are tips to Housekeepers, tips at "comp" hotel Breakfasts, hotel valets, my Times and Journal possibly, and "an extra $20". I'll have the loot "squirreled" over several bags.
Why a hotel Housekeeper's tip cannot be placed on the bill escapes me; that would eliminate the need for $90 of the stuff on this upcoming planned 12 day trip. When I return, second stop (first; PO for my mail) will be the Bank to be rid of whatever is left.
Needless to say, along with any homeowner out there, I have had tradesmen "proposition" me with "could you get me some cash for that?" They are met with a response "I contracted with your incorporated business for the job at this price". That is what their business gets paid, and they are never invited to set foot of my property again.
But I accept. even if I do not agree, with the "other school of thought". This of course goes back a few years as it involves two defunct railroads. I was sent out to San Francisco to do some work (Interline Settlements) at the SP. I was being held out over the weekend (there are worse "punishments" in this life), and this guy with the SP who I was working with said "hey my wife and kids are gone this weekend, can I show you around a bit?" "Sure"; he was a nice guy and we were not really adversaries. He took me out to the Muir Woods and to Point Reyes, then up Mt. Tempallis and over to Sausalito - places I never knew existed or were never going to get to without an auto. Now it's time for Dinner, and expense account be damned, I'm going to pick it up. Well, here comes the check and I have my American Express out. The Waiter returns and I add the tip. My companion then says "can I take care of the tip?", to which I say "all taken care of; it's on the card". He really seemed bewildered, to which I said "holds down on the cash I need to bring" and "this is one tip on which his taxes will be paid". His response to me was "well; that's the best reason I've heard for giving tips in cash".
Nothing further on that point was said.