I just wanted to circle back and share my experience with this. As mentioned before, we checked in May 9th-14th. Apparently we picked a really good week because Aulani was not that crowded (according to the front desk). I had booked the cheapest room directly with the hotel.
Despite what I was told by others and several Disney employees when booking, I was able to upgrade at a reduced price when I arrived. One thing to note, I had already been upgraded to a partial ocean view for whatever reason (it was noted on the email I got to check in online before hand). I decided not to check in online and go to the front desk upon arrival to see what else was available.
Since we went to Waikiki first, we were able to get to Aulani at noon on a Monday. One thing I've always heard is it is best to arrive early in the day if you want the most options to upgrade.
In my typical fashion, I am always as nice as I can possibly be to the hotel employees (and anyone I deal with in retail). I can't tell you enough how the really little things can go a long way. Asking someone how their day is going and being a pleasant human being to others can get you a long way. Some people in this world are such jerks to others and act entitled, and frankly that may work sometimes but that's not how I operate. I have very low expectations on what I am going to get and then I am pleasantly surprised when I get hooked up. I don't expect anything for free and I'm willing to pay. I've worked in retail before, so I know how it goes on the other side. My goal is to connect with the person on the other side, so they want to help me, not feel obligated cause I might complain or get them in trouble.
So after chatting up the front desk lady a bit, I asked her if there were any upgrade options available (please note, these are the exact magic words "Are there any upgrades available". Don't say free, don't say paid, just keep it generic and see what they come back with). She said yes and asked me what kind of room I was interested in. Traveling with 2 little kids, I definitely was interested in a 1 bedroom so I immediately asked about that. She said I could upgrade to a 1 bedroom Island/Garden view for $50/night or an Ocean View for $200/night. I immediately went for the Island/Garden view option and then asked if she could see which rooms would be available where we could still possibly see the ocean. She recommended a certain side of the property (south) and requesting a high floor. This is where the relationship really paid off, she spent a bunch of time explaining the property and where the best upgrade options would be located and looked in the computer for a while about could be available.
I ended up getting super hooked up.
Room 1671, which is the top floor and ended up with a view of the ocean and also where you could see the lawn where they had the Starlit Hui. The one bedroom was fabulous with a full kitchen, laundry and 2 balconies. We also got to people watch on a wedding which was entertaining.
So, if you go on a non-busy week, it is possible to pay for an upgrade at a reduced price and I think I got a great deal on it.
I will say, despite it being apparently not that crowded, I could not imagine going on a crowded week. It would totally kill the experience for me and I could see how it would not be a fun place to be if at capacity. We could still get pool chairs, but it required some looking. Getting a chair with an umbrella was not super easy but doable. We loved the water slides but there was still a decent line (10-20 minutes), it would have majorly sucked to wait in a 30 minute line every time. The property is awesome and the facilities and people who work there are great, however everything was about right. If it was anywhere close to full, the facilities don't seem remotely close to being able to handle that many people without battling crowds for everything. I'd never go back on a busy week, but would consider going back again if we could make it on a off week, provided the weather was good.
