I have never dealt with Michigan Iron, but I've seen their work and read hundreds of posts where they have involvement. For all that I've seen and read, they are an outstanding dealer - experts, honest, loyal, and creative (they make excellent custom add-on themselves for Kioti's). So, I think the 100 miles might be worth the trip. I bought from Wallace in PA when he was a Kioti dealer. He is another of those great dealers. His store is over 250 miles from me. Have never regretted buying from a farther-away dealer. I'd at least discuss price with another Kioti dealer before deciding. Dealer to dealer pricing does seem to vary widely.
On the LS, I know some are concerned with parts, and maybe staying-power. I've been watching them the past couple of years. Over that time they have stepped up their game, filling the void left by Montana and providing tractors to New Holland too. Money talks, and $2K is significant. The free 2nd remote is also worth $400 or so (if you plan to use it). One thing the DK40 has that is real nice is control of the 3ph from behind the tractor. Never seen an LS in person (I do hate the blue). If NH is putting their reputation on them, I have to believe that it would not be bad choice. The risk is if they back away from the market the way that bobcat has done with Daedong (AKA white Kioti). Then your resale value will go down, if they do back away. And it would be worse than BC because at least Kioti is still going strong and can fill most BC maintenance needs. An LS wouldn't have that luxury; I don't see NH readily supporting LS owners if LS backs out as a stand alone brand. Tough call. Kinda where I was 7 years ago when I took a risk and bought Kioti.