I'm getting married July of next year and we're planning on going to Hawaii for the honeymoon. I currently have a Chase Sapphire Preferred and have racked up 100,000 points thus far and hoping to get another 10 to 15 k added by the wedding next July. First thing I wanted to check is how efficient and easy would it be to transfer the points to say United to book our flights? We're going to be flying out of Buffalo and know for sure that we'll have at least one stop over but we'd like to minimize that as much as possible. We've got a few options and I was wondering if people can share their thoughts on what might work best?
1. Fly to NYC and then hopefully take a direct flight to Hawaii
2. Jet Blue just added a direct flight to LA so that's another option
3. Drive to Toronto and take a direct flight from there

I'm trying to figure out other ways to get more points so that I can hopeful pay for most of the flight, if not all, using points. I'm considering Chase Sapphire Reserve but the only thing I worry about is the $4k spending in the next 3 months. I'm not as worried about the $450 fee that I'll have to pay up since they going by calendar years as the 100k in points should help offset it big time. I was reading about some vanilla debit cards I can buy and use Bluebird to repay the purchase but doesn't look like you can buy vanilla cards with credit cards? I'm thinking about buying visa debit cards but can't figure out if I can load that balance on to the blue bird card? Any thoughts?