Jamie, usually the milkweed and butterfly weed (what JB is calling orange milkweed, same thing) grow very well in any type of soil, drought included. BUT, to get them to grow from seed, the seeds must be "cold stratified". That means, as they would in nature, the seeds need to go through cold/damp, then warmer, then cold(freezing)/damp, warm several times. It might be the same thing about the Indian Paintbrush! I'd LOVE some seeds of that.
I looked up the Indian Paintbrush, and how to grow it, and found something I've never heard of before! This is what the site said (JB, have you ever grown it, and if so, is this correct?):
"The Indian Paintbrush needs a good host plant to grow. Good hosts for many hemiparasitic species include low-growing grasses and sedges like Hairy Grama, Blue Grama, Buffalo Grass, Common Oak Sedge, Sweet Grass, and June Grass. With a knife make a 2" deep cut at the base of the host plant. Sow seed in the cut, making sure seed is not more than 1/8" deep. If host is transplanted at sowing time, the cut is not needed because damaged roots will be available for attachment by the parasite. You may also try sowing hemiparasitic and host species seeds together at the same time. To add hemiparasitic species to existing sites, scatter seed on soil surface (rake in if seed is large) in late fall."
And, JB, the only flowers that I grow that are not native, are annuals for extra color and for the butterflies, like zinnias. The queen Anne's lace will eventually take over the dill/fennel/parsley, once I have enough of it established and can show that the black swallowtail butterflies prefer it.

Believe me, I've been working hard to gather more each year! My State has a Native Plant Sale in the spring that I have gone to the last 2 years, and last year I helped transplant the seedlings to bigger pots, so learned a LOT at that outing as well. This year hoping to help out at both transplant dates. So much fun to learn new stuff!!!