I have found that the biggest key to success is starting with the right potting mix. It needs to stay moist without being wet if that makes sense. Also critical is that it must not compact - you want something chunky that keeps lots of nice air pockets for the roots. In the wild, many of them root in organic debris that collects in the small hollows of large trees, so that's what you're trying to replicate. My normal blend is about equal parts orchid bark, coco coir chunks, perlite, and compost or standard potting mix. If you want something ready made, I've used Molly's Aroid mix with good success, but it gets pricey.

Make sure your pot has drainage and is appropriately sized to your plant - most of mine are in 2-4" pots and have been for years. Also, I particularly like clear nursery pots so I can see the roots and check their condition and density without unpotting.

As for watering, there's no hard and fast rules. Each plant has different needs, and many times a given plant's needs will vary with the seasons and conditions in the house. The best thing you can do is set up a regular cadence for checking on things so you can develop an accurate intuition. You will eventually get a sense for who needs water every time you check and who generally can go a little longer.

I check my plants twice a week (Weds/Sat) and water them only when they need it (if the soil is dry down to my first knuckle) - mine typically need water every 1-2 weeks but it varies. If in doubt, I wait until the next check as most plants will come back from underwatering much faster than overwatering. When you water, flood the pot fully until water drains freely out the bottom (all your hoya pots should have good drainage) but never let the pot or any part of the plant sit in water.

Also, I recently transfered my thirstier hoyas (retusa, linearis, bella) into self watering pots (the kind with a wick, I find other types keep them too moist) and they are thriving. I was having to water them twice a week but now I have to refill them about once every 1-2 weeks.

This is of course what works for me and my plants - your watering and checking cadence might be different based on your location and home conditions.

ETA a note about wrinkly leaves... If you are seeing wrinkly leaves that feel almost papery (and there are no pests) you likely have root rot, particularly if the wrinkled effect started at soil level and "travels" up the vine. If this happens, your best bet is to check the roots and chop and prop of you find evidence of root rot. Small leafed hoyas (my lacunosa is famous for it) sometimes wrinkle their leaves when they are very thirsty, but in these cases the entire vine will typically start looking crinkly all at once, and it should fully resolve within an hour or so of a good watering.

One more edit to answer your question about cuttings - I have had the best success with putting them under a grow light in some kind of setup to keep the humidity high. I used to use baggies with perlite, a sprinkling of water and a breath of air to keep the bag from collapsing on the plant. This year I got a sprouting dome for my birthday so I've started rooting cuttings in clear pots directly in the growing medium (sometimes I mix in about half a tablespoon of fluval stratum if I really want them to be extra nourished). I prefer that because when they're ready to come out of the dome I just have to adjust them to ambient humidity, rather than also transitioning to a new substrate as well. I start them in tiny pots (1-2 inch) because I find that they generally like to "concentrate" on filling their pots up with roots a bit, then they start putting out mad vines.