3rd picture is an aphid. Squish it.

Yes you are catching on. The plant still need more sun, and less water, for insurance cut off a stem that is getting roots and plant it. You must realize these are winter growers and not summer growers, mine flower in December and start to grow after the flowers dry up, starting about January, they need air circulation, and cool air, they need soil that drains rapidly, they don't like living in an apartment with a heater going. They are east African plants, and are domant when it is very hot. I have 24 different, so have a little experence. Pirate Girl lives in New York she may have a lot to add to this. I can see that the leaf nodes are still far apart this tells me more sun is needed and less water. Don't treat like it is your pet. Don't water it from the top, water from the bottom, don't mist the plant. No peat moss in the mix, red wood med. size would do much better. I don't normally respond to 'Crassula Ovata' problems any more because it just gets out of hand. Good Luck I hope you will enjoy your plant and stops giving you all of this trouble. The black spots are caused by cultural problems. Gasteria species also haved this problem. Norma

how long do you water 2x a week, also do you have a sprinkler system. they look very vigorous which means they are getting probably too much of something also, some kinds have to be older to bloom better just remember, where they bloom the best, in the Key's, they get NOTHING. you might want to try this: buy bloom fertilizer, mix as per direction and spray the leaves, but don't do it in the middle of the day. i did that with my bleeding heart and it helped to produce blooms.

If the soil doesn't drain well, plant should be re-potted. Ir is always goor idea to repot newly bought plants, since they are often in not-so-good soil, and it also gives you chance to inspect the plants roots. And check for any possible disease. Mix could be very lean, no soil is really needed. Or just very little. You could buy some perlite or pumice, and some grit (best would be about 3-6mm in size). Perlite or pumice should be sifted or rinsed to get rid of dust. Mix them in approx. equal amounts, and add just little soil - maybe 15-20% of total. Aim is to get excellent drainage, so mix doesn't stay wet for many days. Mix like that can be watered more often without staying wet. Any container you use needs to have drainage hole. In the meantime, check your soil using a wooden/bamboo skewer, chopstick, thin wooden dowel (with sharpened end) or even pencil. Stick deep into pot (about 3/4 deep) and leave in for few minutes. When pulled out and is damp, the soil is still wet.