I think it depends on where in Cuba you are vacationing. I have noticed regional differences and apparent differences in the “wealth” of the staff. (also vast differences in the level of appreciation of gifts!) In some areas I gather certain products are difficult to come by…in others, not so much. Money is great…always appreciated…but you know when people want to buy items from you that such items must be hard to obtain (and I’m talking genuine buying here, not someone who hopes you will just give something to them). Some of the items I have found that are appreciated include backpacks, crocs or other shoes, clothing (especially kids clothing), crank flashlights…and one luxury item…Chocolate! Also insulated mugs (bubbas, etc.)
Yes, the resort workers have “hit the jackpot” and receive more than most others in Cuba. However, if you are staying at a resort and someone does you a service that you consider to be above and beyond the call of duty, I see nothing wrong with rewarding that effort in some way other than just handing out cash. If you have an appropriate item (varies with the recipient) it’s nice to do something special for someone who did something to make your vacation great.
Charitable donations are a different animal and require some preparation so that you can get them into the right hands. Just walking, biking or taking a scooter to the nearest town and doling things out doesn’t cut it, as far as I am concerned. Apart from anything else, anyone you are likely to encounter within easy reach of your resort is de facto “working” in the tourist industry…by providing friendly access to their home, possibly a meal or coffee, being “friendly”, chatting to tourists about the poverty in Cuba, etc. etc. For many, this is their “job”, and they make a good living at it! Possibly a better one for less effort than many resort employees. JMHO.
p.s. don’t “dis” the dollar store. I find bargains there for myself!! (often the exact same stuff I see elsewhere for more money)