So, all dooming and glooming aside (don't worry cheerleaders, I'll be back to that soon), I truly believe that a smart GM would trade everyone on the team with less than 3 years of team control left for prospects at this point in the Orioles eternal, groundhog day style rebuilding.
The problem(s) the team has:
1. Complete inability to find talent outside the first few rounds of the draft.
2. Inability or unwillingness to acquire free agent talent of any value.
3. Inability or unwillingness to resign the players on the team who still have a few years of team control left.
4. Farm system is largely barren, and the good players are buried at A ball.
The way the Orioles are positioned now, they'll continue to bring up 1-2 players a year and hope they contribute, while losing 1-2 players a year who are already contributing at the major league level, which results in treading water rather than getting over the hump. The other teams in the division will never stop being good under baseball's current model. The Yankees, Red Sox, and Jays will continue to spend, and all have better farms than the Orioles. The Rays have the best scouting and development crew of any baseball franchise on the planet. All of these teams are better run, have more talent at all levels, and will spend more money than the Orioles will. The current plan cannot work
The solution: Trade anyone still on the team with 3 or less years of team control left.
As much as we love to see our loveable try-hards lose over and over again to teams that simply have more talent, and will for the foreseeable future, the only solution is to try to stock the minor league system with so much talent that it all develops within 1-3 years of itself, and that ain't happening any time soon. Jones, Wieters, Hardy, JJ, Hammel, Gregg, Markakis, and Reynolds aren't part of the future. Don't get mad at me for saying it. It's true. Don't get attached to any of them, because none of them will be here when or if this team is ever competitive. For many of them, their value will never be higher. Wieters has consistently gotten better. Jones is coming off of a career year. Hardy is too. Markakis still has value. Reynolds improved at the plate last year. Jim Johnson is now a closer. Gregg is...well, fine, you got me there.
Trade them all. Their value is much higher now than it will be later on when they get traded anyway but only have 3 months of team control left. Here's a list of what you could reasonably expect to acquire for these guys if you sold them off:
Jones: 2 projectable major league prospects.
Wieters: 2-3 Blue chip, top 50 prospects, maybe more.
JJ: 1-2 projectable major league prospects.
Markakis: 1-2 projectable major league prospects.
Reynolds: 1 decent prospect
Hardy: 2 projectable major league prospects
Hammel: 1 mid range prospect
Gregg: A really good sandwich
Matusz: Mayo, for said sandwich (mustard if you prefer, but it's yellow store brand. Don't get greedy now).
To recap, that's a total of 10-13 guys who are very likely future major leaguers. Right now there's 2, maybe 3 in the system who fit into that category. At least this way you're giving yourself a chance to develop them all at once, instead of bleeding off talent for every prospect you bring up, which is exactly what they're about to start doing in the coming years. On top of that, you're basically guaranteeing yourself the number 1 pick for 2-3 years in a row, at least. How'd that work out for the Nats? Pretty damned well I'd say.
For a team that will not be active in free agency, and does not scout well, this is the best chance they have to catch lightning in a bottle and get a few years of a talented team before they have to blow the whole thing up and do it over again. This is the model that they have to follow, and I hope that they do. The future winning team this franchise fields will have almost none of the current roster on it. Make the best of them while they're here, and use them to turn the team into a winner 5 years from now (if everything goes right).