I find it really hard to believe that anybody tries to lose in order to stockpile picks. This isn't "suck for Luck" at play here. The baseball draft is a complete crapshoot. And even if it weren't, you can't expect draft picks to contribute for 3 to 4 seasons anyways.
It's not so much of a crapshoot right at the top. Picking in the top 7 gives you about a 40% chance of drafting an All-Star, with the rest mostly being useful pieces. Get yourself multiple top 7 picks in a row, supplement that with an above-average scouting system and a clear strategy (hitters bust less than pitchers), and voila. Almora, Baez, Bryant and Schwarber.
And with the current system, the worse your record the more money you get to spend throughout the draft, allowing you more of the lottery ticket-type. And it's not just the draft, having a bad record gives you more money in international bonuses (Soler, Alcantara), priority in waiver claims, etc. That's clearly been the plan of them and the Astros, c'mon man. Spending little or nothing in free agency, hoarding their prospects to try to time them to arrive together, trading away anything of value time and again. They clearly haven't given a f*ck what their major league record was like over the past few years, as long as it was bad and not the worst thing to be in baseball, mediocre.
It's a risk if you do it for one pick, but what the Cubs and Astros have found out is that if you do it over multiple years, it's probably the best way to turn decrepit rosters into talented young rosters who will likely have much more of a chance of competing than tinkering with said decrepity would have. Although, again, the Cubs have done it better than the 'Stros.