The non-waiver Trade Deadline is still a little more than three weeks away, but there has been an acceleration in conversation in a year with so many transitioning teams and, in the American League in particular, such a clear delineation between the haves and have-nots. It could be that things really ramp up earlier than usual, or it could be that the sheer volume of available players compels clubs to wait for prices to fall.
Whatever the case, there are difficult decisions to be made for buyers and sellers alike. Here's a look at seven of the toughest at the moment.
How long can the O's play the waiting game for the "perfect" Machado offer?
Logically, Manny Machado loses trade value every day he takes the field for the Orioles.
Granted, sometimes the Trade Deadline period defies logic. Sometimes desperation sets in. Sometimes an owner or executive wakes up and decides, "This is the player who will take us to the top!" and the offer comes in accordingly.
• O's receive offers from 7 teams for Machado
But in all likelihood, the O's can't afford to drag this thing out in the hopes of obtaining such an offer. Machado isn't helping his market much with his public insistence on staying at shortstop, and recent history insists premier position-player rentals aren't valued as highly as premier pitching rentals this time of year (look at what the Tigers got for J.D. Martinez vs. what the Yankees got for Albertin Chapman).
Presumably, even a lighter trade package would be worth more than the Draft pick the Orioles would receive when Machado signs elsewhere this offseason. But keep in mind that's not always the case. In 2006, the Nationals surprisingly held onto Alfonso Soriano at the Deadline and, when Soriano signed with the Cubs that winter, wound up doing pretty well with the comp pick (Jordan Zimmermann).

Should tax and Draft penalties deter the Red Sox from certain deals?
Beating the Yankees in the division and avoiding the potential one-and-done Wild Card round is pivotally important for a Red Sox squad in a World-Series-or-bust frame of mind. But quite often, improving your roster in-season means taking on salary (with so many transitioning teams, executives are speculating that this could be a trade period especially heavy on salary dumps), and there are serious ramifications should the Sox pad their payroll this summer.
With a payroll projected by Cot's Baseball Contracts at $233.75 million, the Red Sox are already well north of the luxury-tax threshold, which means they are paying an additional 20 percent on every dollar north of $197 million. They are actually in the second phase of the penalty structure, which means they are paying another 12 percent for every dollar north of $217 million. An additional increase past $237 million would result in a 42.5 percent tax on all overages.
Maybe, to the Red Sox, the tax is no concern at this point. But the third penalty phase also calls for a club exceeding $237 million to be docked 10 spots in the first round of the 2019 Draft, and that's a big hit to any ballclub, especially one with a farm system that isn't as deep as it used to be.
Should the Dodgers' past inform their present?
The Andrew Friedman regime has been reluctant in recent years to part with prized prospects and take on significant salary in the trade market. In many ways, it's an understandable approach. But it's also why they ended up with Yu Darvish and not Justin Verlander last year -- and we all know how that turned out in the World Series.
The Dodgers' payroll, according to Cot's, is roughly $187 million right now, so just $10 million shy of the luxury-tax threshold. To be clear, the payroll, as calculated for luxury-tax purposes, incorporates average annual values, bonuses, benefits and other expenses, so that's not the exact figure. But the point is that the Dodgers are close enough to that dividing line to complicate their place in the Machado sweepstakes and other deals. They need bullpen help, and they possibly need starting help and/or a bat to win the West again and get back to the Fall Classic. They have incentive to do things economically, but they have recent history to demonstrate what can happen when the big-ticket assets go elsewhere.
Should the Yankees pay the steep price for a controllable front-line starter?
Well south of the tax threshold and in possession of one of the deepest systems in the game, the Yankees are simply in a better position than their Boston counterparts to get an impact deal done. But their effort to improve their rotation behind young ace Luis Severino is met with a market relatively light on impact. The Yankees can overwhelm rivals in the bidding for guys like Cole Hamels and J.A. Happ but might be better-served in the short- and long-term to go after higher-upside, controllable types like the Mets' Jacob deGrom or the Rays' Blake Snell.
• 5 starters the Yankees should consider
Brian Cashman is unwilling to move Gleyber Torres or Miguel Andujar, but he'd quite likely have to change that tune to get such a deal done. As good as Torres is, the Yankees are arguably a better October 2018 team with deGrom than with Torres, even though they are quite possibly a better team with Torres than with deGrom in the long run. Theo Epstein and the Cubs understood they were, in all likelihood, "losing" the trade in the long run when they dealt Torres for a rental of Chapman, but their '16 World Series title insists it was worth it.
As the Deadline gets closer and the East battle rages, could Cashman find himself willing to do something similarly drastic?

How aggressive should the Indians be with the division in hand?
Spoiler: The Indians are going to win the AL Central. Heck, they might win it by 30 games like they did in 1995. This gives them the option of bottom-feeding in the swap market.
Keep in mind, though, the Indians have a .683 winning percentage in the weak AL Central but a .455 winning percentage against everybody else. They have the longest championship drought in the game. They have expiring assets in the bullpen (Andrew Miller and Cody Allen) and in what has been an injury-riddled outfield (Michael Brantley). They have the positional flexibility of the great Jose Ramirez to play with in a market deep with third basemen. So while the Indians don't have the same in-season urgency as the game's other contenders, they do have some organizational urgency to make a proper push.
Do the Braves need third base help, or nah?
The Braves are definitely looking for controllable relief help in their effort to maintain their momentum in the National League East, but they are also oft-cited as an obvious landing spot for one of the intriguing names available in a market deep on third-base options. The arrival of an impact player like Machado, Adrian Beltre, Mike Moustakas or Josh Donaldson (if or when he's healthy) would fire up the Atlanta fan base even more, but is such a move even necessary?
Johan Camargo began the year hurt and then lost playing time to Ryan Flaherty and Jose Bautista. But he's settled in nicely at third, with a .287/.345/.481 slash since the beginning of June. The Braves should leave no stone unturned in their effort to fend off the Phillies and Nats, but this might be one stone they can leave alone.

Should the Angels buy or sell?
Teams like the Rockies, Giants, Cardinals and Nationals are no doubt disappointed with their standing, but at the moment it's still hard to craft a compelling argument for them to sell, given the competitive conditions in the NL (this sentence is very much subject to change, of course).
It's different in the AL, where the Red Sox, Yankees, Astros and Mariners have set the bar for October entry abnormally high. The Rays have been friskier than expected but are still far more likely to sell than to buy (indeed, they've already moved multiple pieces this calendar year). The A's are on pace for upward of 90 wins but have a similar organizational track record as the Rays and might not be inclined to aggressively chase their faint hope of a Wild Card berth.
The Angels are a little different story, if only because they entered the season with legitimate October expectations. Expiring assets like Ian Kinsler and Garrett Richards don't have much trade value right now (Richards only came back from injury this week), so not selling might be an easy decision at the moment. But what about buying? Run differential insists the Halos should be right on the Mariners' heels, not trailing them by double-digits. Now that Shohei Ohtani is at least back as a DH, should the Angels put any faith in that factor and hold out hope that the M's come down to earth? Is this team worth propping up in any meaningful fashion?