I'm higher on Latimer and Eifert than you are, then. I've got Latimer as valued somewhere around 1.06, Eifert as valued somewhere around 1.08, and then a random first on top of that. So that's a mid 1st, a low 1st, and a random 1st. Future 2nds aren't half as valuable as future firsts, either. Like I said, I'd prefer Calvin over that package. Change Latimer into Evans or Watkins and I think the two sides are about even. Or turn Latimer into Cooks and replace Eifert with another 2015 first. As it currently stands I think that's more of a good starting point for negotiations than a good ending point. But if that's the best the Calvin owner could do, I've got no problem with that.
In a startup, I think the idea of trading a very high pick for a series of mid-round picks is underrated. Maybe I'd be looking to trade 1.02 for a trio of 6th-8th rounders instead of a trio of 8th-9th rounders, but again, I think the basic thought process is fine.
History suggests that the odds of both Eifert and Latimer hitting are less than 25%. One is going to bust. Even if the one who doesn't ends up being a top 10 WR or top 3 TE (far from likely)--is the gap between that and Calvin only a 1st and 2nd?
I liked your 4 random pick study, but I see a few major flaws: There is no such thing as a truly random first round pick; roster spaces (spread out over 2+ years, no less) are very valuable; most importantly, even if history shows you'll eventually break even or better, it's still not the most efficient way of getting there.
For example:
Calvin for Alshon, 1st, 2nd
Alshon for Cobb, 1st, 2nd
Cobb for Cruz, 1st
Cruz for Beckham, 1st
Beckham for 1st, 2nd
That's 5 1st and 3x 2nds, using only deals I would consider pretty likely to be accepted--I think one could easily turn Calvin into 6 first rounders in a sequence like this.