Dombrowski's been pretty good at trading away minor leaguers for actual MLB talent (e.g. picking up Doug Fister for peanuts). And the issue that Detroit has with the draft has bit all the big market clubs in the ass in recent years. Well, except Boston the last couple of years because their FA signings all got injured after the '13 title and the new ones have flopped.
One thing I will say about Dombrowski, he's really good at acquiring major league talent, which was Ben Cherington's weakness. Cherington made a horrific decision last year amidst the injury apocalypse to deal Lackey and Lester for major leaguers rather than prospects, and then getting major leaguers that weren't equivalent talent. E.g. by not striking early and raiding the A's farm system for Lester they ended up turning a #1
starter into a #4
/5 starter, similarly they turned a #2
/3 starter on a bargain contract into a highly paid position player whose career is over and a pitcher that can't throw strikes. If he'd dealt Lester for Addison Russell instead he'd probably still have a job (because Boston would be starting Russell/Bogaerts on the left side and they don't tie up all that money in a guy that's rapidly eating himself out of Boston). Getting minor league players out of the Cardinals would have left him in better position to trade this year.