We bottle because we have a reason or goal. The reason can vary for each of your wines.
* as Bob said head space increases the oxidation risk. Oxygen creates off flavors, on a few weeks sharp notes like apricot and loss of fruit notes. With extended / over a month expect a burn when swallowing total loss of fruit and sometimes petroleum like notes. , , , Bottling to reduce head space is a good reason.
* for carboys with about an inch head space clarity is a good reason. In essence we sulfite and move to smaller bottles which are appropriate for consumption in a few days or a meal. Again oxidation is a big driver. If you used bag in box you could keep it in one container, traditional Italian house wine is in a crock with a floating lid. Back to clarification, young wine will have small particles below visible that continue to settle after bottling. It doesn’t taste, just looks bad. You can be careful pouring and avoid this.
* red grape / fruit with tannin has binding between tannins and protein, these settle making gunk, (sometimes called natural so don’t worry). Waiting months to a year lets more reactions happen and the gunk is gone when you bottle.
* northern grapes have high tartaric acid which crystallizes when chilled. In whites this is a sand. In reds more brown gunk. This again is cosmetic.
* convenience is a big reason. Bottle when you want to use it so that oxidation is minimized.
Wine is a preserved food system. Your down side is cosmetic. Your up side is serving size containers resist oxidation / retain flavor better. Neither of these are health risks, ,,, so in a way the end answer is bottle when convenient.