Remember that semps are very hardy and love being outdoors. But they are alpine plants and long stretches of blazing heat is not to their liking. But they deal with it OK as long as they have moisture. I don't know about your particular climate, but some southerly regions like Texas, Arizona and New Mexico are challenging for raising healthy semps.
In general, rely upon your own general plant knowledge. Plants that look healthy and happy generally are. Plants that look like they are dying generally are.
#1 - Keep an eye on the lower rows of leaves. Are they getting mushy? That could mean rot, which is usually fatal to the individual rosette. Are they drying up and crispy? That could mean that it is having water issues which could be due to root issues. Semps should feel solid to the touch and firmly anchored in the soil. Soft floppy leaves or wiggly wobbly rosettes is trouble.
#2 - semps are not cacti, and can take more water, even in cool weather. But, as usual, in cooler weather they require less moisture. My semps are in moist soil 365 days a year, but it is well draining sandy soil. Pots are difficult in that they can be bone dry at the top but moist at the bottom. One strategy is to add small amounts of moisture regularly at the top knowing that it won't sink down so much and get the pot's bottom saturated. You'll have to find your own way of making sure your semps have moisture available regularly while avoiding soggy soil that could lead to root problems.
#3 Shake off the soil that came in those pots. If you lose some roots doing this, no problem. Spreading roots out is fine. Trimming them is also tolerated. Semps have vigorous roots that can replace themselves quickly. Some people root prune severely at transplant time. I would take it easy in that respect, although plants are often happiest when spreading new roots.
#4 Planting high I'm guessing means that you keep the leaves off the ground. People will sometime tuck gravel under there to keep the leaves high and dry. Sounds like you're doing likewise.
#5 Chicks usually pop out in April-June but can happen anytime during the growing season. I generally wait until chicks have roots on them, even if those roots are just hanging in the air, before harvesting a chick for planting. But I have received small, rootless chicks that grew roots nicely when planted. If the chick is showing a rosetted form, then it's likely mature enough to transplant. Now is a good time for chick harvesting and planting. They should grow happily with warm temperatures, adequate sunlight and adequate moisture. Remember that their roots may be extremely short so keeping them moist will help them establish.
#6 The chicking habit you're describing is sort of normal. It's not the usual way, but it seems any semp during any year might do this. It's weird but normal and not to worry about. Although it can be inconvenient.
