Do what you feel comfortable with.  As long as it's American I don't care.  And the bank won't notice.  They don't care that I deposit cash regularly.

The bank won't care, or even notice, unless your withdrawals exceed government reporting requirements (which I believe is $10,000 in a single day), in which case they must report it.  I frequently withdraw large cash amounts that have nothing to do with the hobby and don't exceed the government limits.  The only time it ever came up was a few months ago when I withdrew twice in the same week with the same bank employee.  She said something to the effect "I see you're back again" and we both laughed.  I also doubt that the lady will care as long as the envelope contains the correct amount.  When participating in longer engagements, I will usually include a few smaller bills, as a matter of courtesy, in case she needs to tip a valet at the hotel or use it for cab fare.  Do your research and have safe and happy hobbying!

You can look up large deposit/withdrawal guidelines for cash. I believe it's $10,000.00 and above that become reportable. Withdrawing a few hundred dollars every once in a while is nothing! Large or small bills (I'm answering this based on source of withdrawal), the only difference is that on a bank statement one will show up as an ATM withdrawal and the other will show up as a branch withdrawal.

It could be argued by others that a businessman or someone needing to buy something legitimate off of craigslist would go to the branch, whereas someone involved in drugs wouldn't have the wherewithal to plan accordingly and therefore need a 'last minute' ATM withdrawal. Both this argument and the opposite is bullshit.

It's your money and no one will care. There are other reasons people would want to withdraw cash that are perfectly legal. Maybe cause a smirk, but legal nonetheless. You could have a 'healthy' strip club addiction. Hourly rates there are very similar to the hobby. It's your life, and privacy is very valued in this country. Don't worry and don't be paranoid about this. If you have an SO (I don't) worry more about that than what bank employees would do.

I accumulate funds in advance.  "Big bills" are not so big anymore.  I just ask the teller, no big deal at all.  
You might have a cover story if you feel you need to, like a large private purchase.  Buying used cars or equipment, I always pay cash.  Load the car & go.  
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It does not make a difference. Jacksons, Grants and Franklins are fine.  They all spend.

I can only say that when I have made some rather large withdrawals in large bills, several times, the bank supervisor/manager was called over to endorse.  That always made me uncomfortable, but there have no problems so far, and the transactions were never large enough to require paperwork to be filed with the feds.  This issue is further exacerbated by the fact that most banks have a rather low limit on the amount that can be withdrawn at any one time, or any single day, from their ATM's.  Curiously, that limit does not apply if you use a credit card.

From what I have seen, the ladies don't care whether you use Jacksons, Bennies, or Grants.  But if you you doing longer engagements, Bennies and/or Grants are the way to go.

One other thing...we hobbyists should be willing to share info re: ATM's that dispense in larger bills.  These were once relatively few, and the only ones now that do are in casinos, from what I have seen.  

I think they would prefer you gace them a Cleveland or Madison without change back. Still better would be a Woodrow Wilson. I'm sure she will be very happy with that. It might take some explaining though.

I am not picky..either will do..thanks