I agree, this is my pattern.
When I travel or my kids do independently I always go to the bank and make sure for my travelling I have taxi fare, taxi tip, sky cap, DME driver, bell services, bell services again if I need blankets or more pillows, trip worth of tip money, again in reverse, bell hop, DME, taxi money, taxi tip. If you are going to use bag check in when departing don't forget to tip these people who take your luggage too. When I check my luggage through DME to be delivered to our room I always leave a tip marked for Bell Hop who delivers my luggage. This time I got a thank you note on the piece of paper I wrote Bellhop luggage tip on. (being clear is important when leaving money) I also ordered different pillows and another bed blanket, on the same table I left the tip for housekeeping on the same table also marked for them.
I leave the house for vacation with a separate envelope in my backpack where I have about $30 singles, $5, $10 and $20 and two $50's for my taxi to and from airport 'cause nobody really wants to drive me to the airport at
3am. That envelope usually has about $200.00 in broken down cash for specific purpose and then goes in room safe. I also for 10+ trips carry about $750 in cash or cash between us 'cause ya never know. I also buy when I get to Disney a gift card for about $100 or so where I can hand it off to a cart vendor, someone in our group or cup cake vendor, glass of wine from a kiosk etc. where I don't want to be dragging out my little wallet. Take a picture with your phone of the gift card back with code numbers once activated. (note for those who don't use magic bands, if you are using a media ticket, special events tickets, take a picture of those backs too with your phone in the event they are lost those numbers make it easy for Disney to track and cancel.)