Addicted to gardening & plants for decades, moved to AL from OH in 2007 and absolutely love it! My passion is beautiful and unusual foliage inside and out, nectar plants for hummers and butterflies, fragrant flowers, propagating whatever, and attracting the (friendly) tiny critters like birds, anole lizards, toads, hummingbirds, butterflies, geckos, skinks. We don't use any sprays or 'cides.
"This plant likes to be rootbound" Oh, this is sad!
No plant likes to be rootbound. What is necessary for plants to stay alive is for their roots to not rot, which can happen so easily in a pot with airless soil. Having very little soil around the roots would make the soil dry more quickly, and for even the most dedicated plant-overwaterers to not rot the roots of their plants. This is not ideal, since most non-cactus plants are stressed by dry conditions, it's just a way of coping with soil that has little air in it when moist.
Negative experiences in regard to potting-up, where an undisturbed root ball is placed into a bigger pot with more soil around it, vs. doing a repotting, as described below, can give rise to old wives' tales about plants not liking to be repotted/disturbed. Potting-up a root-bound plant that has roots surrounding the outside root ball often lead to this negative experience because those roots had adapted to accessing oxygen around the outside of the root ball and surrounding them with more dense, soggy-but-airless potting soil will likely lead to suffocation.
The reason bonsai masters are able to keep potted entities alive for hundreds of years is because they care for the roots by trimming them and changing the soil. A plant grows from the roots-up, so if the roots are not healthy, gorgeous foliage will decline &/or no flowers can form. When you unpot a plant and find a pancake of roots at the bottom, chopping that off will give roots a chance to grow normally again for a while and will make removing the old soil easier.
Roots need oxygen & moisture at the same time to function. Just air = shriveling. Just moisture = suffocation & rotting. Either will cause root death and desiccated foliage because the roots have been unable to deliver moisture. Having to let soil dry, as if ones' tropical jungle plant was a cactus, is an unnecessarily stressful coping mechanism for non-desert dwelling plants in soil without enough oxygen for the roots to stay healthy when it is moist and can lead to premature loss of older leaves and in extreme cases, dry shriveled roots/dead plant.
Please know that any resource that prescribes a schedule to water your plant is not worth taking seriously because it's impossible to predict how often a plant will need water. A Dracaena marginata can be a tiny thing that is just a few inches tall, or a much older entity that is taller than a person. The bigger plant will use a lot more water. Throughout the year, the usage could vary. Plants don't take a drink periodically like humans, the roots are constantly at work to obtain moisture and deliver it to foliage, so some moisture must be present at all times.
Factors like temperature, humidity, air movement, amount of light, size of plant, size of root mass, size of pot, type of soil, type of pot, and vigorousness of a particular plants' metabolism all play a role in the speed at which the plant is using moisture, and the speed at which the soil is drying.
"Overwatering" is under a hyped-up emphasis lately. This occurs when moist soil has insufficient oxygen in it. Roots need moisture and oxygen at the same time to function, and to not suffocate and rot. There are ways to ameliorate the risk to virtually none.
Because I have so many pots, I can't give specialized care to each one or check them before adding more water. I just water all often enough so that there is never a moment when the soil has no moisture. I haven't had a plant die of rotting roots ("overwatering") since I quit using potting soil with peat in it, and many plants have been moved from plastic pots to clay pots. Clay pots allow oxygen to penetrate the entire surface of the soil, not just the top, so plants can enjoy consistently moist soil without having the roots rot.
At this time of year, all of my pots are outside, where it's 95°, so they need water about every-other day. If I waited 2 weeks, most of the plants would be dead. But when they are inside over winter in cooler temps and a lot less sun, some plants only need more water after about a month.
In addition, when repotting, don't pack the soil and water gently the first few times until the particles lock in place so the soil doesn't compact. The little air spaces will further eliminate the risk of rotting roots.
My most sincere hope is to never arrive at a point where I think I know everything. I doubt that's possible, and would be too boring to tolerate.