I haven't ever spent any time trying to eat acorns. I know it can be done, and have heard all about boiling, roasting and other methods. I do have a solid recommendation:
Experiment with the SPECIES of oak/acorn and your success will be dramatically different.
As a very committed hunter I've eaten a LOT of browse. I'm continually tasting various kinds of mast crops (apples, acorns, etc) trying to figure out why deer ignore one wild apple or oak but completely go insane for another. It's taste.
Red Oak: A red oak is a beautiful, fast growing tree. Animals will eat red aok acorns but these seem to be the least preferred. If you taste them these are BITTER! I can well imagine that these would take considerable work to reduce or eliminate the tannins.
White oaks: These are somewhat less bitter. Deer seem to prefer these. I suspect because they have fewer tannins. Less tannins in the first place would likley mean less work to get an acceptable, palatable end product.
Burr Oaks: These are, I believe, one subspecies of the white oaks. There are a half dozen or more different types of burr oak. They all drop an acorn with a 'fuzzy' cap. Some burr oak acorns are HUGE. In any case, the burr oaks are know for having 'sweet' acorns. This doesn't mean they are actually sweet, but rather do not have the distinct bitterness that other oaks do. The tannins levels are low. I was scouting my realestate on Friday, and checked out the various oak ridges. Little recent movement in the red and white oaks, but I have CRAZY levels of wildlife activity in and among the bearing burr oaks. I cut acorns open and shared them with a friend. They are actually palatable and can be eaten raw, without preparation. He claimed they tasted remotely like coconut. Actually these are so good, and so desireable from a wildlife standpoint that I am ordering several dozen Burr Oak saplings for spring transplanting into hardmast food plot. Some of these burr oaks have been bred to produce large crops of low tannin acorns, reportedly on the order of 500-1000 lbs per tree.
You can find some interesting (as far as trees go) info at a few sites. Websearch "sweet acorns oaks" or the like and you'll get info regarding which oaks have the lowest tannin levels.
Burr Oak source
If you scout around and locate the oaks in your area, pay attention to specific species and cultivars (yes, oaks have been and are being bred). There is a HUGE difference in palatability.
Frozenny