Lets talk steak

Don't bother shelling out a ton of cash if you're going to cook them above medium rare.  Hate to be judgmental of someone else's preference, but you're cooking out all the benefits of high-end steak at that point.  There's always a temp rise after you pull, so shoot for 5-10 degrees under your target temp.  120-25 for medium rare should work fine.  If you're doing a reverse sear, you shouldn't be going as high as 400 for the initial portion of the cook.  Try to keep the temp in the area of 275 to bring the internal temp up.  If you're dropping the steak into a spider on cast iron for the final sear, definitely don't do two minutes per side.  That's going to overcook them, as you rightly pointed out. I'd go a minute per side tops if you're putting it in the spider on cast iron.  With flank and skirt steaks, top of the fire ring direct is fine, but you should go higher than 400.  Try to get to around 600 and sear each side for about two minutes.  You might want to do this on cast iron; it'll create better carmelization.  Don't bother with a reverse sear for cuts of meat as thin as a flank or skirt steak.  Just sear the outside and call it a day.  In fact, for any cut under an inch thick, you probably don't want to reverse sear.

Here is my $.02.  When you are doing a reverse sear- don't bother trying to take the temp during the sear.  Measure the temp during the roast period and once it reaches the desired temp let it rest while the grill heats up for searing.  The steak is basically cooked at this point and you are just trying to put a crust on it.  You may want to check the temp to ensure it has stopped rising from carry over.  Get the grill nice and hot, and only go about 1 minute per side.  Like @bicktrav said doing this on cast iron works great as well, especially for thinner steaks. 

I sometimes wonder if someone who wants a steak well done really wants a steak to begin with.  I mean, are they sitting there thinking, "Oh god, I can't wait to sink my teeth into a nice well done steak", or are they really thinking "Well, if I have to have steak, make it well done so I don't puke."  If it is the latter, I think I'd make the effort to cook them something else that they really want to eat.

I think some people are just scarred to have a steak any other way than well done. I have been slowly getting my wife to eat med, med-rare steaks. At first she was really hesitant but after a little prodding, and possibly a little bending of the truth on what temp the meat was cooked to, she is much happy with the taste.