How to deal with the amount of acorns that fall alongside the leaves is the biggest problem when approaching the actual vacuuming of oak leaves. If you have considerable sized oak trees then come the colder months, they can leave quite a considerable amount of leaves and acorns in their wake - and in your yard.
Vacuuming Live Oak Leaves
The simple answer to the question "will a yard vacuum work on live oak leaves?" would be "no" - not if they are accompanied by acorns in any great number. Even the best yard vacuum motors, would be open to damage coping with acorns as well as live oak leaves. So if removing acorns, as well as oak leaves is your dilemma, then you would be wise to seek some suggested alternatives.
Portable wood chippers with a vacuum ability, would be a definite viable alternative, to using a yard vacuum for live oak leaves, with a large number of acorns amongst them. The biggest drawback of this is that wood chippers are much more expensive than yard vacuums, and may not be a viable option if you only want it to remove leaves. It may be worth looking into stores that offer wood chippers for hire.
Consider a Leaf Blower
A common alternative to a yard vacuum is a leaf blower. The upside of using a leaf blower is that some models are often a leaf blower/yard vacuum in one. So although the vacuum feature may not be a useful one to use for live oak leaves, you could use it for other yard jobs, and the leaf blower feature, would be a perfect solution to dealing with the masses of leaves that will clutter your yard.
The downside to using a leaf blower, of course, is that they simply move the leaves around, rather than removing them. You could use the leaf blower to blow all the leaves into one place, making it easier to pick them up and remove them. Or you could blow them out of the way, making a path alongside a driveway or edge of the garden, and leave them there as a mulch for your grass, over winter.
Other Ways to Deal with Clearing Oak Leaves
After considering the "fors and againsts" of how to vacuum live oak leaves, or using a leaf blower, you may be ready to consider some alternatives to the oak leaf problem.
As live oak is such a hardy tree, it is easy to forget that it too, like any tree, needs caring for. Pruning is even necessary on a live oak, up to the age of about 30 years. Live oak trees should be pruned every year, for the first three years of its life, and then every five years after that. If it's been a while since your live oak has been pruned and it's under 30, then now may be the time to start pruning. Not only will it help improve your trees structure, it will also minimize the amount of the leaves that will fall.
Remove the acorns, before setting to work on the leaves with a yard vacuum; old-fashioned raking. Make it part of your garden routine in the fall and winter months, and keep on top of it by raking the oak leaves every few days. You can make use of the leaves as mulch, or put them in the compost.
You could alternatively look for yard vacuums that do double duty -- some work as shredders too.
If you are wondering how to find the time to vacuum those pesky live oak leaves yourself, then consider getting in some garden help for these jobs - leaving you time to concentrate on the more pleasurable side of gardening.