If Tavares leaves Isles I do not see him going to a team without a solid D with a PP quarterback type of D and he will not opt for a team without a proven goal-tending duo. There are the slight possibility that his family may convince him to take a discount for his home town team or his agent may advise him on taking the best term ($, term, NMC) but if winning the SC is foremost on his mind, he will pick a team with a stable balanced roster with goalies highly capable of winning the SC, with location and contract terms rounding out his decision. What happens within the next three weeks in the NHL including all complete trades may heavily impact his decisions. I do not think at this stage the draft (order or who got drafted) will have any impact on his decision. I am a big Tavares' fan, but he is not Crosby nor OV. He likely cannot and knows very well that he alone cannot carry a team to the SC final. He would need a solid team, top notch goalie performance with a very strong system to do that. Yes, he has carried his team to the playoff before but the grinding 16 games where opposing team can focus on shutting you down offensively each game will be a tough run for him. He has a good shot but not the type of quick one timers that can break open a game on PP. In fact he need to go to a team that has an elite shooter and a very smart D quartering the back end both on 5 on 5 and PP. I know JT's game, he is strong on stealing pucks in the offensive zone and he has ability to cycle well and set up players in the open or near the net. He plays best with teammates who can onetime the shot accurately or who can consistently get to the front of the net, fight off the D and complete the shots.
I also do not see that he will be the best fit for Toronto as that team's biggest need is on improving their D and I believe their number one focus this summer will be acquiring a true #1 or #2 D via trade or UFA. They have plenty of offensive talents but without key contribution (both offensively and defensively) from the blue line they cannot succeed in the post season, let alone winning the SC.