Take on the resort fee

Obviously I am not highbrow and nothing is more apparent that i don't belong as when you put me in a resort. I basically have no idea what I'm doing in a situation like this and find myself stumbling all over myself when it comes to etiquette
Take this place with their $20 resort fee which should make part of it easier but instead makes it much more difficult

I get it as a concept as I am never sure how much to tip, when to do it and how much us appropriate. It ruins an entire vacation for me as I spend every waking moment questioning myself and in theory this resort fee should make that easier but for those of us with no knowledge about it, it winds up costing you more
But what should make is easier actually makes it more difficult because nobody can explain who and when to tip.
Take yesterday when the bellhop brings my bags up and then spends 10 minutes explaining everything about the resort As he gets ready to leave my room I reach into my pocket and only see a $5. Now it seems like this is too much but I feel completely weird about asking for change and the guy is obviously stalling for something
I bite the bullet and hand him the finsky. He smiles and thanks me and then tells me that the resort fee covers incidental tips. The problem is that he already has the five-spot and I can't exactly ask for it back. So now I feel like I'm screwed twice. First for overtipping and them for not knowing what the resort fee is supposed to cover. I have to say that this is the kind of thing the front desk should make abundantly clear when you check in

Now my buddy the Bump who has worked in the service industry for most of his life and thus throws around singles at a hotel like Righetti at a strip club, probably doesn't find himself in that spot First of all like a trip to FD'a he probably walks in with a 6 inch stack of singles so even if he didn't know about a resort fee he'd only lose a couple.