Got a bit of a quandary in a H2H keeper league I'm in, entering its second year. We're down to 14 from 16 teams last year, so a couple of premium players are re-entering the draft pool (Beltre, Fielder, Darvish, Strasburg, Rios, Bautista...). Keeper rules are such that anyone drafted in the first 5 rounds that you keep will slot in to the first available pick, anyone from Round 6 onwards is kept at a 2 round penalty. There's no limit on the number of players you can keep.
As of last year's finishing positions I'm picking 7th (and then 21st, 35th, 49th, etc). I've no idea what strategy the other managers will be employing on keepers, but I suspect a fair few will be quite conservative and keep more than they should. Most of my keepers are no-brainers - I've got Braun in Round 1, Bailey with 105th pick and Arenado with my 203rd, for instance.
If I wanted to keep Carlos Beltran, though, he'd have to be a fifth round (pick 63) which I think is a bit too high (I have him in the 80s). A couple of others that are closer to my rankings but would still be a reach are Lucroy (133rd) and Frieri (175). I know Grey will be down on Lucroy that high, but he's just an example from my later rounds to illustrate my point.
I guess my question comes down to rather than "would you keep x player at y spot", but what extent should you be prepared to reach and go with the known quantity, or how much should you trust your own rankings and not overpay?