-- Sunday-Wednesday will be Park days, Thurs-Sun conference then in afternoon ? Park vs beach vs ?
Five days is the greatest number of days you can buy tickets for -- Sunday through Wednesday is 4 days, so unless you're going to buy another ticket for lots of $$, you'd only be able to do one more park day. When we stay at the DLH, we usually do a pool day/DTD night.
-- On those parks day would you take advantage of the extra hour?
We always do the extra hour. As long as you're ok with getting up that early, I say yes.
-- Would you use a planning app like touring plans or Ridemax?
I always use these apps, but never use them exclusively or stick to them religiously. I think they're good to get a general idea of what you want to do. Once in the parks, I tend to use Disney's own app more, especially since they've come out with MaxPass. Which is another thing I would always use.
How bad will the crowds be? I get it’s summer. Just curious if it will be Wall to Wall? For comparison I’ve been over Candlelight Weekend.
-- Haven't been over Candlelight Weekend, but we went this same week last year and it wasn't awful. You definitely have to do some planning, or if you're not a planner, be aware of a general order you need to do things in to avoid super long lines. I do think it's important to be there at opening this time of year because it makes a big difference when it's crowded. And we always head back to the hotel from about 2 til 5 or 6 because it does start getting more crowded (and hot) at that time, so it's helpful to decompress. My teens disagree.
--Are there “not to miss” things at the hotel (other then Trader Sams)?
Last year DD17 and I did afternoon tea at the DLH. She really enjoyed it. We also enjoy sitting by the fire near Frontier Tower in the evening. And watching for characters in the lobby if you're staying in the Fantasy Tower. If you have young kids, they play games at the pool in the afternoon.
I’ve never entered DL by monorail in the AM. Is it a good plan? Or is rope drop better?
-- We always do rope drop. The monorail doesn't start running until park opening, so it gets you into the park later than it would if you were at rope drop. We always try to do Peter Pan first and if we took the monorail we'd never make it. We often try to take the monorail back to the hotel mid-day, or take it when we go back to the park in the early evening, although I've often found it's down or has such a long line that it's not worth it.
-- Specific to hotel... please tell me the beds are comfy lol.
I don't have a memory of this one way or the other, so I assume they must have been!

The headboards are cool.
Anybody ever reserve a cabana?
-- Yes, we reserve a cabana on most trips. The pool at the DLH can get really crowded, so this is something I really enjoy having. It's SO convenient to be able to lock your valuables in the safe, get out of the sun if you want, and be guaranteed a lounge chair! Service is often very slow. You can bring your own food and use the frig they provide. They give you a fruit plate for free, but it's pretty dull, like apples and bananas, and several times they've given us bad fruit. You can order anything off the DLH menu, even if it's not on the poolside menu. They have someone from room service bring it out.