The plants I'm thinking of keeping in pots are oriental poppies, hollyhocks, foxgloves, balloon flowers (or do these bloom first year?), painted daisies and several others that critters in this area like to gobble up before they get big enough to plant in the garden.

Thanks! :)

One challenge is to keep the young plants alive over the winter in small pots. I usually group them closely, surround with bags of leaves and cover with a thick layer of leaves. Or bury the pots in the ground in a garden bed. I lose a few plants each winter, but most survive.

Also you can pot up seedlings and plant in fall. These were my Foxglove plants from last year which grew on in pots until getting them planted in September.

Pennisetum alopecuroides 'Hameln'/dwarf fountain grass from winter sown seed

There's a winter sown Montauk daisy in a pot on this table

This is that Montauk daisy:

I suppose when you think about it, isn't that how they do it at nurseries? Grow them in gallon pots and keep them there until they are big enough to sell?

But that makes sense to just move them into larger pots as they grow larger. The only thing I can see at this point from what all have shared here that might be an issue is keeping them over winter. I think I'm going to play it by ear and see just how big they are by fall. I imagine things like hollyhocks would probably do better if planted in the ground over winter.

I over-wintered lots of perennials inside my garage the past several years and haven't lost anything so far. They all go dormant so around Thanksgiving I start bringing them inside the garage for the winter. Once the weather begins to warm in the spring, they all push up new growth as if they'd just awakened from a long sleep.

As with anything else, find what works best for you given your own unique situation/circumstances/climate. Experiment and keep notes/a diary of what works and what doesn't. I keep a garden diary from year to year which helps me get acquainted with the plants in my garden, what to expect from each and when.