If I was fast forwarding to the summer (not something I particularly want to do with 15 games of a fun season still to come....9 of which are at home.....but that seems to be the crux of this thread), I think the order of business would be this:
1) Find out early what offers are on the table for Dickie and Brannagan. With just 12 months to go on their contracts, we will surely sell if we receive offers for either above 2m - and possibly will take any seven figure offer. In the unlikely situation that noone's in for either of them, offer them new three year deals on good (for League One) terms. But anticipate that we will lose them both.
2) Found out what's going on in Eastwood's head. If he really wants out, allow him to go. As a 30 year old keeper who's had minimal experience above League One - he has negligible resale value.
3) Offer Sam Long a new one-year deal. No he's not a world-beater, but he's a valuable, versatile squad member and he's worth the wage. Pick up the option on Ruffels
4) In a worse case scenario, that leaves us with a squad of Long, Ruffels, Moore, Atkinson, Jones, Gorrin, Henry, Hanson, Sykes, Hall, Forde, Napa, Agyei, plus some other youngsters. That's the beginnings of a strong defense, a decent midfield already ready to go and not a whole lot going forwards
5) [the most difficult bit] Find and sign half a dozen talented footballers aged 20-24. These could come from lower leagues, non-league, Ireland, Scotland but given the contacts of our management team, are most likely to be academy graduates of clubs higher up the pyramid who haven't quite made it. We've developed an amazing pipeline over the past five years or so, from a variety of places (Lundstram, O'Dowda, Roofe, Ledson, Rothwell, Baptiste, Brannagan, Dickie, Johnson, Whyte.......) but we need to continue to fill it. Some of these may cost small fees......so be it. We should be reinvesting a proportion of the proceeds from our successful sales.
6) Add 3-4 high calibre loans from Premier League clubs to fill out positions of need, and round out the squad.
Until we sort out the infrastructure of the club, including securing ownership of our stadium, so that we can capture all revenue streams and sustainably grow the club - the above is the model that's working for OUFC. And KR, and his backroom team, have shown themselves to be great at it. No reason to believe that they can't deliver another fun season in 2020/21 that way.