Hey, I completely understand your point and can totally agree with it. I just (totally my opinion) don't think Riley or Davidson will be ready until 2018 at the earliest (Davidson) and have always like the player Desmond was. Again, this was just an "outside the box" idea. No matter what, we have to find Freddie some protection and that could be Riley/Davidson/Ruiz/Olivera but the FA market is slim until 2018.
No question. That being said, signing someone like Desmond/Upton is just not the "smart thing to do". Would that make the 2016 and 2017 lineups a little better? Sure. However, doing so significantly makes you less flexible in the future.
Look at it this way - signing either of those "sexy" names would seemingly add that 20+ HR right handed bat you want behind Freddie, no question. The problem with either is...
1.) You have to play Olivera at 3B if you sign Upton (or even Cespedes or Byrd for that matter)
or
2.) You have to play Desmond at a position he's never played before (Aybar's not Andrelton by any stretch, but he's much better equipped to be an everyday SS than Desmond), whether it's at 3B or in LF.
Either signing makes you weak at 3B defensively - don't do that if it doesn't make you substantially better or competitive (when you're not really trying to be to begin with), especially when you could go out and get a Byrd-type who could give you the same thing without giving up anything that could help you in the future.
Desmond or Upton would be a far-sexier sign (no doubt), but neither of them does much for you considering where you're trying to go. They'd both sell several more thousand tickets over the next couple of years, but the salary you'd pay them would more than soak that up - PLUS either would cost you a draft pick that could be FAR more valuable in the long run.
Don't get me wrong - I'm all about "outside the box" thinking (pretty sure I'm the first one who proposed trading any of Andrelton/Julio/Freeman) - but doing so has to come with clearing the books in 2017-2018 in mind so you can spend where you deem it's important. I completely understand (and share to a certain extent) the skepticism many have about the organization eventually playing at the top of the market again, but EVERY move they've made in the last two years has been made with the thought of keeping that option open. They're going to "break the bank" on the international market this July, and signing or trading for players to "fill holes" over the short-term (Markakis, A. J., Aybar/etc.) falls right in line with that philosophy.