Den. Spring Doll 'Sweetheart' HCC/ADS winter rest/keiki's
 

As you can see this orchid has grown like a weed in the Spring after a nice rain! It's a monster! My question is about winter rest; how much water should I be giving this orchid so that it lives but also so that it blooms better in the Spring, last year, one flower, I did not know to rest it in winter then. It is very root bound and as you can see there are some Keiki's which need to be addressed. Should I wait until after the winter rest to cut off the keiki's and repot or can I do it now? When is the best time to remove a keiki from an orchid? Thank you for your advice!

I usually remove rooted keikis in the early spring, whether they are snowing new activity or not.

Seedlings & keikis typically require less of a rest than mature plants, which typically need it to initiate buds.

Nice plant! Looks very happy and healthy. Not knowing your conditions it's impossible to say exactly how and how much to water through the winter, but as a general rule moniliforme and hybrids heavily derived from it neither need nor appreciate a totally dry winter. I water my similar plants sufficient to keep them from shriveling in the winter, which varies depending on temperature, light, air movement, humidity, mount/pot and potting medium, retention or not of leaves, etc...

IMO cooler temps are the more significant blooming cue, with moisture playing a secondary role in that signaling chemicals may build sooner to critical concentration at bud sites when the plant is less hydrated. Give your plant 2-3 weeks of night temps in the 50s F or lower (my plants of this type tolerate overnight lows below freezing without problems, though YMMV), make sure it dries well between waterings, and you're likely to see some blooms in the spring. Hope this helps! :)