I was looking in to see if there is a clever way you could setup an automation to do this for you. But perhaps the easiest will be to create an annually repeating work order for each month of the year (unfortunately this is not an elegant solution). 

The repeating steps can be setup as individual procedures that you can then use as building blocks embedded within each other to make your life a bit easier. In our case the start and end of each preventative maintenance work order is generally the same. So we use this same principle for that. Then at least when you edit the procedure it will simultaneously update all the work orders that it is used in. So one procedure for the steps to take during the monthly check. Another procedure for the additional ones to add when doing the quarterly check and the monthly procedure embedded within it. And a last one for the additional steps that only appear in the annual one, with the quarterly one embedded within it as well. 

You will need to create four individual quarterly work orders, each set to repeat once a year. After creating the first one, you can use the ellipsis (3 dots in a vertical line) in the top right hand corner of the work order to “copy to new work order” so that you don’t have to recreate the whole thing from scratch. You will then setup one to repeat once a year during Q1, the second to repeat once a year during Q2 and so forth. The annual one you will luckily only need one of. The monthly one will then require only 7 individual work orders to cover the remaining months of the year. 

Personally I would use the calendar month’s name in the work order title along with indicating whether it is a monthly, quarterly or annual check. If you setup each of these to also repeat once a year, you will be covered all through out. 
It may feel like a lot, but utilizing the 3 procedures and the copy to new work order functionality will make it quick to setup, and after the initial setup you will not have to worry about it again.
Sorry this is a mouth full! If anyone else has a better solution, I will also be learning something new!

The way I have set ours up seems to work.

I have individual work procedures for Weekly, Monthly, Quarterly, Bi-Annual and Annual. Each will only have the necessary parts for that time of service, not the others. On the longer ones they will have a line stating to assure the lesser PM’s are complete. So on an annual it would have a line stating something to the effect of “Assure all weekly, monthly and quarterly PMs are completed.” Then as they are done they can log the appropriate time to the appropriate PM. This adds time to the signoff at the end, but keeps everything separated and sorted. It seems to work well as long as the individual work orders are closed as they are completed.

​@James Beers Your method works but relies on your team to ensure they complete as many as 5 different PM’s in the proper sequence. using your example above I might create an all-inclusive Annual procedure that rolls all the other periodicities into it. The first step might be to have them sign off all the other PM’s due for that asset (Weekly, Monthly, Quarterly, Bi-Annual) with no time and reference the Annual PM work order. I just need to figure out what works easiest and the craft will use.

John