I definitely am not a fan of giving up draft picks though there is obviously a difference in doing it for Harper/Machado/Corbin as opposed to Rheal Cormier.
Part of the failing of the old administrations is that they did not compensate by spending more to sign fliers late in the draft when it was permitted to do so. This is why it is important to max out our young talent by dealing for competitive balance picks or additional international money. I think we only dealt for about half of what we can so we likely won't max out on that this year. And next year the teams under penalty are over so it will be more expensive to trade for international allocations.
If we do sign free agents with lost draft picks this year it would probably be a good idea to direct a couple of trades for young prospects. If we get Machado, we should be able to get a prospect for Franco for instance that would be the equivalent of a lost draft pick. Same with Harper. We should be able to get talent for either Herrera or Williams if we no longer need to fill major league roster holes.
What we never want this organization to lose sight of again is the need to constantly replenish young talent. Money can be used to help do that. We failed in that a decade ago. Now hopefully Klentak is smarter about that aspect of organization building. We now have a midlevel system. It could become poor relatively quickly if we don't start adding some talent again. The cumulative effect of lost draft picks and missed number ones could catch up in a hurry.