If we use someone to service the machine, who’s money will be in the machine? Does the cost of servicing increase depending on how often it is serviced (filled) and how much money is put into the machine on a regular basis?

The cash will be provided by you. Yes, the cash services usually charge by drop. This cost can change based on geographic area, frequency and provider. Typically you would want to keep a little over a week worth of cash in the machine. This figure can be determined by your current payouts.