Hope the first one is the RFA signing of Dobson, who is the key piece for Isles to build around for years.
To build a team you need to bring certain pieces one at a time. When not much is available out there, then you sometimes do pay a premium to fill a hole. When they trade for JGP, the team needs a premium PK player who is strong on the faceoff with speed. The one best fit for that need at that time is JGP, although I am not quite happy about giving up a 1st for any player unless it is for a proven top 6 or a top prospect. JGP had played well but got hurt in the playoff and had an off year the following season.
Lee is a player they could not afford to not resign at the time they sign him, they do not have anyone like him in the system - a strong front net presence, a good captain, and who can score goals.
The Seattle expansion and lack of prospects ready to push out older players due to a bad combination of top entry draft pick by Snow's scouting team) and Ladd's contract did not help. Lou inherited a lot of Snow's problems which limited his ability to improve the team further. Now he has some of his good young pieces, he needs to be patient and hope to improve within, even if that meant another bad year to get some higher picks to enable him to fill out the holes either from within or improve future trade options. Most teams improved got their big piece from finishing bottom 5 - right? TML - got 2 major pieces within 2 consecutive years, Oilers (similar). Avs, and Tampa, where did their top players come from? Even Rags got lucky and landed two top picks recently and their top goalie was drafted, not acquired via trade. Which team that won Cups recently did not benefit from getting top-notch performance from players drafted from positions 1-5 in the first round?
However, Isles can't go the rebuilt/retool route the last few years as they brought in a respected top coach and need repetitive playoff success to keep fans coming back in a small market competing with 2 other teams in the same area. The owners bought the team with goals to make the team competitive each year to improve the value of the team in short term, not over the long term, in order to recover the hefty investment they put into the team in a reasonable time span. If they only can be patient with giving another 4 years, they can field a more competitive team from drafts, as that is normally the time to take to acquire enough good prospects and turn those assets into a more entertaining and cap manageable roster.
UFA signing typically means overpaying on terms, unless the player had an unimpressive UFA year, major injury concern, and hence has gotten very few competing offers. Offer-sheet rarely happens. Isles had arena issues for years and finally, they got a beautiful one built but unfortunately, they are stuck with cap problems. I am not saying Lou did not make some bad choices, but some are made for reasons he could not control and a big part of that is the lack of young prospects especially gifted speedy natural goal scorers in the position of D and C in the system, to push out players no longer contributing consistently.