Give Point a 3-year bridge deal with the cap hit of $7,25M. Make it a backloaded contract, resulting a high qualifying offer in order to make it more acceptable for Point to take on his next contract.
Point deal breakdown
2019-20 - Base salary: $700k + Signing bonus: $5,425M = Total salary: $6,125M
2020-21 - Base salary: $700k + Signing bonus: $5,425M = Total salary: $6,125M
2021-22 - Base salary: $9,5M with no signing bonuses, making the total at $9,5M.
That would be the qualifying offer as well if I've understood correctly.
Also move the goalies and one of the assets that might need a bigger contract next year, try to acquire a rental asset for playoff run.
For 2020-21 season...
About signings...
Anthony Cirelli - using Alexander Kerfoot as a comparable, making it a bit cheaper due to TB being leaner of taxes and whatnot. Also taking one year from the deal. $3,25M at 3 years.
Mikhail Sergachev - using Darnell Nurse as a comparable with a $3,2M at 2 years contract.
Erik Cernak - I'm taking a guess that TB GM tries to make Labanc with either Sergachev or Cernak - 1 year deal with minimal cost, and then promise that his next deal become much higher. In this example, it's going to be Cernak. 1 year deal at $1,5M.
Alexander Volkov - 2 years at $1,05M. Contract that of like Adam Erne, provided his next season goes close to such as he performed.
Other prospects get signed to either $750k 2 year deals or $700k 1 year deals.
With these signings, only Alex Killorn must be traded, provided that TB decides to only use 21 man roster. Witkowski works as a reserve player pretty well as he's fit to play either 4th line grinder or as a d-man. Killorn's NTC becomes M-NTC with 16 team trade list at July 1st, meaning that trading him gets much easier.
If TB gets to the 2nd round of the playoffs, the 2020 2nd round pick converts into the 2020 1st round pick. If TB gets to the SC finals, the 2020 3rd round pick converts to the 2020 1st round pick. In that case, NYR receives 2020 1st and 2nd round picks.
Just making a wild guess that EDM might have a good slot for Killer. Their wingers are pretty bad and a solid 40-point winger with a lengthy contract might slot in well in their roster.
Should be trading Sergachev .. Cirelli #1 Cernek #2 Sergachev #3 and Josepeh/Volkov #4 for 2020 .. not hard to see one of Joseph/Volkov will be gone with Killorn but 1 of other shrimps needs to go OR trade Sergachev and keep Killorn .. at 4.4M AAV he best contract where Gourde the WORST
OF COURSE .. if Tampa craps the bed again .. Stamkos HAS TO GO!!!!!