Wow, so many suggestions! Thanks so much everyone!
All are good points. From the photos my contractor sent me it seems like a small issue, but from talking to him he seems to think its a bit issue. Either he's trying to upsell me or there is more going on then the photos are showing.
I may need to fly down there and check it out myself. First, I'm going to see if we can do a video chat and have him show me the issues closer and then I will make my decision from there.
Side notes on comments, a few people brought up the self leveler and fillers etc. The only problem with using regular self leveler or any concrete product is that the floor is suspended on floor joists and will have a small amount of bounce and give. After a while that concrete will break up under the vinyl plank. I have heard of flooring guys mixing in Alex Plus with the water mix to give it elasticity which is an option. I was thinking of using an acrylic based wood filler (advise from a contractor friend of mine) so that its flexible and sandable.
@Joshua Howaniec Believe it or not, the sand under felt does work. I did some free work for a missionary base that was installing laminate flooring in an office that had the most atrocious sub floors you've ever seen. They didn't have the finances to go the self leveler route as it would have needed about 40 bags. I let them know about the sand option and they wanted to go for it. I layed the laminate (not vinyl plank), it felt solid at the time. 1 and a half years later went back to visit and its still as solid as a rock. I'm not a big fan of hacking, I'm just saying that if your in a pinch, this one works. I wouldn't do it for vinyl plank though, its too flexible.
@Brian Pfaehler What is the drum sander you're talking about? The only drum sander I know of is usually fixed in a woodwork shop and is upright. Could you send me the name of a product or a pic please. I'd be interested in trying this out if I go the acrylic wood filler route.
Once again, thanks so much for taking the time to lend me your experience! I hope you guys all profit well in the coming years and that you can avoid hurricanes like I had to go through!
On that note, If you don't mind me giving some advice from my latest experience, I recommend that all of you go back to your insurer and ask them to do a Marshal Swift analysis on your property to see if you are adequately insured. It takes them some time but only costs them $18. This is the same program that underwriters use to screw you over, so if you have the analysis in your files then they are bound to fully insure your property if needed.