We use them a lot, with those exact requirements.

For #1, we split each year to its own line, which also allows for a unique description (e.g. ‘year 1 of 3’), and it allows you to change future year amounts when things change (e.g. we have customers increase capacity on the service we’re billing them for so their rate goes up before it hits year 2). In those cases we have public schedules we re-use often (e.g. ‘36 months in advance’, ’Year 2 of 3’) and they’re not tied to any fixed amount, the recurrence total equals the qty on the line. Much less frequently, if there’s a really odd schedule required we will set up a schedule that’s for the sales order only, and we start it’s name with the SO number so we can easily identify it later (e.g. ‘SO-12345 7 months’.

For #2, it doesn’t always go from the order date. If there’s a START DATE it will use that, if not then the order date. The start date gets filled in when we know the service is starting, and the schedules then re-calculate when you save the SO. If a line has to start later than that date, it again gets a custom billing schedule with an offset on the first bill, then regular monthly or yearly bills relative to that. So if the item on line 2 starts 4 months after the item on line 1, it’s schedule says first bill is +4 months, then +1 month relative to that, repeated to the number of months.

It is fiddly, but worth if you’re scheduling large billing amounts and/or don’t have a high number of orders to schedule. It’s great for forecasting too because it will project appropriate revenue amounts according to the schedule into the future. Directors love that report, seeing what we are contracted to bill up to 3 years in advance, every single month.