[EDIT] - Updated with Salary Arbitration deadlines

Yup. Sounds like a spy novel from the Cold War era with a touch of "The Troubles" in Northern Ireland. No doubt a New York Times bestseller.

What I'm attempting to do here is to set up the negotiating positions of the Avs and Ryan O'Reilly's camp for his upcoming contract. I'd like to outline possible strategies and how they will change as critical dates come and go. I'll then take a stab at how it might all end.

I'll also give a shout out to GeorgeInLimbo whose Fan Post on the O'Reilly situation got me off my duff to finish this.

Now until February 28, 2014 (Anniversary of the Offer Sheet Match):

CBA says...
The Avs cannot trade O'Reilly before the one year anniversary of matching his offer sheet.

Avs position and activities:
The Avs will be attempting to get O'Reilly's agent to answer the phone and kick off negotiations. At the same time, the Avs may start shopping O'Reilly to potential deadline partners. They will have a very short window to complete the trade, so they'll want to grease the skids.

O'Reilly position and activities:
It is likely that the O'Reilly camp will solicit an opening offer from the Avs, but unless it offers both salary and term close to their satisfaction, there is unlikely to be a response. Essentially, they are countering with the RFA Qualifying Offer (1 year at $6.5M).

Best case scenario:
This is the time where both sides could show a willingness to work together and have both sides happy with the result.

Probable result:
Based on O'Reilly's hardball tactics last year, the one year anniversary of the contract will pass with no extension.

Open Trade Window (March 1-5, 2014):

CBA says...
The deadline to complete any trades where the players involved will be allowed to play in the playoffs is March 5.

Avs position and activities:
The Avs will field multiple offers for O'Reilly. They will probably communicate those (more unattractive) offers to the O'Reilly camp, and re-iterate their prior offer, possibly with a little sweetener. This is the time when the Avs have their maximum leverage (they can send O'Reilly to Buffalo, for instance), so expect them to try to get a contract signed.

O'Reilly position and activities:
If O'Reilly is serious about playing hockey for a contender, he will likely counter with something less than the RFA QO, but with a term that will make him qualify for UFA at the time of his next contract. If he's only in it for the money, this period will pass without a response - again countering with the QO.

Best case scenario:
Hopefully the added urgency of the trade deadline gets both sides to the table and they hash out a deal.

Alternate scenario:
If a contract is not forthcoming, and the Avs find a willing trade partner offering good value that fill areas of weakness on the roster, O'Reilly is gone.

Probable result:
A trade is a serious consideration as O'Reilly might be a valuable asset to a contender, or a key building block to team on the upswing. It's unlikely that ether side will change their negotiating positions substantially, so if there is no trade the trade deadline will pass without a contract.

Trade Deadline to SCF Conclusion (March 5 through mid-June 2014):

CBA says...
Not much.

Avs position and activities:
There is little to be gained and plenty to lose (distraction) by negotiating through the end of the season and the playoffs, so it's unlikely that anything will happen. I would expect the Avs to have a quiet period at the end of their season, and contact the O'Reilly camp to see if they wish to counter prior to the Salary Arbitration deadline. As the deadline approaches, they'll start shopping O'Reilly again. O'Reilly is unsigned, but as an RFA his rights will transfer.

O'Reilly position and activities:
Play out the string.

Best case scenario:
Both sides discover that they really want to stay together and a deal gets done.

Probable result:
Not much.

48 hours after conclusion of SCF (or June 15, if later):

CBA says...
If a team intends to file for salary arbitration, it must do so within 48 hours of the conclusion of the Stanley Cup Finals (or June 15, whichever is later). O'Reilly is eligible for arbitration as he has 4 years of professional experience and makes more $1.75M (plus a smidge to account for the increase in league average salary). In arbitration, the arbitrator can grant no less than 85% of the prior year's salary. If O'Reilly gets an Offer Sheet from another team prior to the arbitration hearing, this all goes away, and the Avs have to again decide whether to match or take compensation.

Avs position and activities:
If the Avs intend to take O'Reilly to arbitration, this is the date. I think if the Avs select arbitration, O'Reilly is not long for the team. They can only do this once in a player's career, and it generally creates acrimony. Are they willing to poison the atmosphere for less than $1M? If they do, they will be fighting to improve O'Reilly's trade value by lowering the value of his next QO.

O'Reilly position and activities:
Watch and wait.

Probable result:
I don't think the Avs take O'Reilly to arbitration unless all prior negotiation has been not only fruitless, but hostile.

Monday after NHL Draft (June 29, 2014):

CBA says...

In order to receive a right of first refusal or draft choice compensation in the event of an offer sheet from another team, the Avs must make their qualifying offer (QO) by 5:00 PM Eastern Time on the later of June 25 or the first Monday after the NHL Draft, meaning June 29th in 2014.

Avs position and activities:
The Avs probably tried to trade O'Reilly's rights during the draft, but were likely unsuccessful. At this time they must submit an offer sheet of at least O'Reilly's prior year salary (plus bonuses) with a term of one year to retain his RFA rights. If they choose not to, O'Reilly becomes an Unrestricted Free Agent on July 5.

O'Reilly position and activities:
If it's gotten this far, this is probably as good as the offer gets from the Avs. They've been angling for this since the trade deadline.

Probable result:
The Avs submit a QO to O'Reilly and the League.

NHL Draft to the opening of Free Agency (June 29 to July 5, 2014):

CBA says...
A player must file for player elected arbitration prior to 5PM Eastern Time on July 5 to qualify.

Avs position and activities:
Watch and wait.

O'Reilly position and activities:
Unless O'Reilly had a ridiculously good conclusion to the season, it's unlikely that he'll gain by arbitration over the QO that's on the table.

Probable result:
Nothing.

Free Agency (July 5 through ???):

CBA says...
If O'Reilly gets an offer sheet from another club, the Avs have the right of first refusal to match that offer, or receive draft pick compensation from the new club.

Avs position and activities:
Watch and wait.

O'Reilly position and activities:
O'Reilly's agent will be actively working the phones in an attempt to secure an offer sheet for his services.

Probable result:
Since Jay Feaster is no longer a GM of an NHL club it's unlikely that a better offer is put on the table, and O'Reilly signs his qualifying offer prior to training camp, and we get to do this again next year. I don't see a big hold out like last time. As we can now see, that holdout happened while Feaster and O'Reilly's agents were negotiating the offer sheet. All the rest of Meehan's clients signed their QOs and reported.

TL;DR version:

If O'Reilly is still an Av after the trade deadline, it is likely he stays with the team on a 1 year $6.5M contract and we get to do this all over again next year. Don't fall in love kids. Until you see a multi-year deal, he's not a part of the core and will be traded before he qualifies as a UFA at age 26 (7 years experience).