Nope!! Once they are outside for the season (if not winter hardy) then they stay out for the entire season. But since the vast majority of mine are permanent and hardy plantings, they stay outside year round regardless of the weather.

Overwatering issues are obviated if you use a properly fast draining soil mix :-)

I use a 5-1-1 mix for all of mine so I think I should be fine with the watering then. How about the strong winds? Can that possible break off some branches of my plant or damage them in some other way?

If your plants are in very well draining mix, they can be rained on quite a bit. Typically, I don't find regular rain to be too much/causing overwatering. Many days of non-stop rain could be too much, and you could cover them with a plastic sheet. Do you have such rains regularly? Wind could be a problem, it would blow off anything and blow over the pots. It happens to me with bigger plants sometimes, and I try to keep them somehow secured - few pots close together, tied up to a post, heavy rocks on top of soil and so on. Very strong winds are more of problem and you may have to bring them into some shelter. If plants tip over, there could be some damage.

Succulents could be more sensitive to overwatering. What plants are you growing?

I have 11 different conifers seedlings with sizes ranging from 15-30 inches. The smaller the plants=more damage? I also have 2 citrus

The conifers will tolerate wind easily, even very small ones.

I don't know anything about citrus (do not grow any), but have few small conifers and np - agree with gardengal.