After reading the few comments regarding use of a skewer the most common (but not all ) comments suggest to water when the skewer is dry. I'm not the wooden stick poke in the pot to water type never have been and never will be nor do I favor the when in doubt you don't water. Lesson to learn is a growing plant does need more water in comparison to less water(ing) when it's not growing. In a sense to say let the plant tell you when to water not a stick or a meter Haws are pretty easy they tend to get use a regular watering regiment depending on the type of Hawothia ,it's growing season and the conditions it's growing in. Cacti of the pot cultivated ones here vary from one type to another some will get heavy watering regularly through out the year from year to year some will wait for a while. jades, echeveria are closely related and are somewhat opportunistic they can last a while with out a drink during the slower growing ( rest) times as long as the rest conditions are correct the rest time can last for several weeks.

Mealy bugs. Spray with 50% isopropyl alcohol/50% water, (or 100% alcohol as it evaporates better in a humid climate) daily for a while. You need to get the eggs as well as the adults, and new hatchlings will appear for a while (and thereafter, so keep the spray bottle handy but out of reach of kids). Do not spray with the plant in full sun--it can burn the foliage. Some prefer systemic pesticide. That works too, but not everyone wants to use a pesticide.

You could try putting the sprout end of the leaf in dark, i.e under coarse sand or some other substrate. You could also use a rooting hormone, or a branching hormone. You can get both from a hydroponic supply...not recommending this, just saying it is an option. Rooting hormone is something I use a lot. it generally does produce roots in harder to root plants, and faster roots in those that are not hard to root. it also increases root growth on leaf props. But the issue with some reluctant echeveria leaf props is that many will produce roots, and then takes years to produce a plant bud. I have a few that are firmly rooted into their pots, have been for over a year, still waiting to see that little guy poke up.

Nice plants, but they have different care requirements so they're not good candidates to put together. Ex: Haworthias prefer indirect light to part shade, while Crassulas want as much direct sun as they can get. Personally, I'd be more concerned to get them out of that peaty looking & mix into more appropriate soil.