Leonard is at an age where he needs to be tested sooner or later, so he needs to be looking ar the Championship.
If he enjoys it down there and/ or has some ties then I'd possibly stay for the final year of his contract. Each month fron now on whilst he's playing well then his valuation goes down but his salary demands at a new club go up.
The situation can be reviewed in January18.
If Southend are top 2 at Xmas then it might be worth while staying at Southend to see if they get promoted.
But if Southend are mid table then I reckon he'll be sold in the JTW for a knock down price of £100 to £200 K
And due to the smalllish transfer fee then it gives him a great opportunity to negotiate a big pay rise at a Championship club.
Or he could see out his final year, massive risk for Southend but no risk for the player.
Leave on a FREE in Summer18 and get a pig pay rise somewhere else.
It wouldn't make much sense for him to sign a contract extension at Southend as this means he could spend his whole career in the lower divisions. Just because the Sothend Chairman might be ambitious doesn't mean promotion. We have an ambitious Chairman with relatively big finances and we still spent 6 years in league 1.