A legitimate shot is having Miggy signed and in his prime, at least one ace (formerly JV, then Scherzer, and currently Price), then having some other shiny pieces like Victor, Iggy, Cespedes, Soria, Kinsler, and so on. You can always build around that core and make a run. Most of us worry about when the core disappears though. That will happen at some point (3-5yrs?) w/o some level of rebuild and/or consistently solid drafting though.
The Tigers lost $20.7 Mil last year and are expected to exceed that amount this year. They have lost money in 5 of the last 7 seasons (-$90.1 Mil in those 7 years), soon to be 6 of the last 8, due to "because Illitch will do anything to win" theory. DD has traded away virtually every prospect that meant anything the last two years and this year's draft was another of the same, i.e. picks no one else would draft as high as the Tigers. Last year's top pick, Derek Hill, is almost a complete bust.
It takes 3-5 years for drafted players to be able to make any contributions at the big league level. Longer for High Schoolers. Hich Schoolers are also the most volatile picks, as they tend to fail more often than 2-4 year college players.
Top 75 picks by DET
2009 = 1 HS (Turner) and 1 4YR (both traded)
2010 = 1 HS (Castellanos) and 2 4YR (both have been traded away)
2011 = 0
2012 = 0
2013 = 3 4YR (top 2 were traded away)
2014 = 1 HS (Derek Hill) and 1 4YR
So, in the 6 drafts, Detroit has had 10 picks in the top 75. Of those 10 picks, they have traded away 6 of them. Aside from the two players from 2014, they still have Castellanos (possibly a bust?) and Ziomek (too old for the league he plays in).
The top pick in 2015 is a High Schooler, Beau Burrows.
Again, the cupboard is bare and their recent drafts suck. You get most of your better MLB players from the top 60-75 picks. Occasionally, a team drafts a Mike Piazza in the 62nd round and gets lucky (currently MLB only has 40 rounds).
They cannot spend more money and "fix" the mess. At $172.7 Mil payroll is already $9 Mil more than last year. They are on track to lose $30 Mil this year, more if they miss the playoffs. Adding another high priced player means that go further in the hole.
By not turning a profit, they do not have the money to invest into player development, like most of the other teams do.
We are all Tiger fans and want them to win the World Series. Heck, I wished they have won more than they have. But I have lived through the lean years and I would rather not do that again at the sake of a slight possibility. This team needs serious help.