When are you ready?

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You need to research what others charge in your area and use that as a guideline. Every part of the country/world is different. There can also be a huge difference in parts of the same state. I'm sorry but there is truly no easy answer. We have all wrestled with this quetion when starting out,regardless of the type of photography.
Best of luck and enjoy the journey

Portrait prices are fairly high - $50 for any size smaller than 8x10, $100 for 8x10 to 11x14, and $200 for everything larger wouldn't be unreasonable. Anything less than that is you having low prices to start out with, or a different business model. Professional pPortrait photographers don't sell or give away digital files - if they did there's no way for them to make any money.

What do you think your time's worth? What do you think it's worth for you to bother doing prints? Prints take a lot longer to do than you expect, especially if you count the ordering process, processing, uploading, checking, reprinting, packaging, and sending them out.

Just remember they are not just paying to reimburse you from the lab. They are paying to for your photography through the costs of the prints. Unless you charged an hourly rate, then you may want to consider a more reasonable rate for the pictures, IMO.

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Don't plan to do it... just do it.

Sit down now and figure out your cost of doing business, only then will you be able to establish a pricing structure to cover that and give you some reasonable profit.

Do the best you can with your predictions. But be aware you can adjust things later, as you become more experienced and find things that you overlooked or that are costing less than you thought, or if your costs change.

In tandem with this, yes, you need to get a solid idea what the competition is charging and how they structure their packages, services they offer, etc. Very important you not be too high or too low.

You can offer discounts for your services, as a new business. One way is to offer some percentage off in exchange a signed release that allows you to use the photos taken in your own marketing and advertising. You might also offer something for referrals, if you wish.

You're ready when you're willing to do what it is necessary to set up a business on the up and up. That means paying taxes on what you make, getting business insurance, getting a contract, and putting together a business plan.

The photography is secondary and is usually the fun part. If you have the business know how and acumen, then you'll have the effort it takes to learn the photography craft well.