Your plant looks lovely
It is good it is by a bay window, since it loves as much light it can get. Flowering phase is normal at this time of the year, and does not mean it is stressed. It just means your growing area has ably met the conditions it needs and plant is mature enough to make blooms.
I cannot see clearly how many jade plants are in there. You may want to consider in mid Spring to repot them in separate containers, that way you will have a more defined tree that you can ably make quarter turns as needed to even out light distribution.
But it is your choice..I am not sure if you truly intended that manner of growth. Each grower has their own goals.
But just for example..I do grow jades, and thankfully our area is a mild winter area so it can grow outdoors year round, rain or shine. Typically I only have one or two trees in one container. But one is more than enough per container since it naturally would grow upright and branch out as it seeks as much light and heat it can take.
Crassula ovata
Crassula ovata 'Gollum'
So consider doing some pruning in mid Spring. I do not see a problem with your watering style. As long as there is no soggy part in its trunk or branches then all is good. And quite sure you already are aware the plant naturally sheds older leaves as season changes.
If you do repot later, as usual make sure to use gritty, well draining media, container with drain holes. Just callus the cuttings and then plant later.
Good luck and keep us posted how it goes.