It would help me to give you the proper recommendation if I knew wether you were going to buy these with your own money or if your unit was going to purchase them for you.
I have no experience with the 5.11 boots but I have a great deal of experience with the Oakley assault and desert assault boot.
bottom line up front: NOT WORTH THE MONEY if its your money.
If you buy them from the Oakley military sales program, you can get them for as cheap as 75 bucks and then they are OK. I saw kids in "the pipeline" that were paying full retail $225.00!!
The boots are soft and comfy but not suited for "field use". They are not water proof and are a giant sponge if they get wet. They retain water/sweat for a while which causes them to stink to high heaven over time. I had to sleep with mine outside of my hooch downrange and I live alone!
The construction is also not very good as well. These are not "boot, Jungle-OD, with spike resistant sole, 1ea. They are not going to last you more than a few months of everyday use in a harsh environment. I took and brand new pair downrange and the inner liner had holes worn in it in less than 90 days.
These were designed for people that wanted an "assault boot" thats what it is, people that use it for missions other than short duration Urban DA will most likely be disappointed. The designers also did not really care about long term durability because of their ability to DX the boots for new pair for free anytime that they want to. I know guys that are going through 8 pair of Oakley boots every 12 months on the high end.
If you are paying out of pocket, I hope this helps you make an educated decision about how to spend YOUR money...cheers.