We didn't lose the Segura trade, because Santana was included to take his money off the books and then give it to Cutch, similar age and production, but Cutch was a far better fit than Santana - and highly durable, his injury was a fluke.
Build a solid core, resign Realmuto because a top catch is important if you want to build a good pitching staff, and he should have 5 years left as long as they don't overwork him. The league is catching up to Alfaro b/c he totally lacks plate discipline when selection is favoring pitchers who can deceive with offspeed stuff around the K-zone.
To me, the first use of money is to lockup the starting lineup, including extending Hoskins early at a higher rate rather than having to pay him to 35+ years old. Segura I'd let play out his deal if Stott looks ready in 2 years.
Realmuto, Hoskins, Kingery, Segura/Stott, Bohm, Cutch, Haseley, Moniak, Harper isn't a bad start for 2020-2025 or so.
Build a solid bench around them and you should be among the league leaders in run scored every season.
Then you look at spending on the pitching staff, but looking at the minor league system, I think Klentak has made it a priority to stockpile arms, including lots of RP candidates. Given the track record of veteran RPs, I'd be looking to go with youth as much as possible - when Arano goes down, it doesn't park $10-20M on IR.
I'm wary of giving ANY SP a deal longer than 3 years unless the cost is low enough (Nola) that you can eat it without distress. In today's game, a record of durability no longer predicts future health, in fact, being a top pitcher with high velocity who has a few 200 IP seasons almost seems like the kiss of death, it's the guys who learn to throw without velocity like Grienke and Kershaw who seem to last forever.
I'd rather trade for high priced veterans with only a couple years left on their deals and spread money around the Morton's and Smyly's each year and eat the money for the ones who don't work out (and give attractive bonuses for veterans to go to AAA ball and show they've recovered/fixed to the point of being able to pitch in the majors again). To me, pitching is basically about "safety in numbers," we've seen too many pitchers crash and burn.