Depends on where the points are down at.
If it's mostly single position training, even if you plan on training it, then it takes longer to path the person out. If he's a PG with 2 OD and you are training OD already for 10 weeks, then he'll at best end at an 8 OD, which isn't ever good enough in d2, nor is it good enough for D.III. In addition, in order to get to something borderline good (15 OD), 26-27 weeks is a likely amount of weeks for OD (2 seasons). In such a case, i would default to someone i can get more miles out of, if the second guy is 6 OD thats at least half a season less training single position to get him to the minimum requirement.