Really appreciate all the helpful info!
I'm staying at the Diplomat this coming Mon-Thu for a work-related conference, and decided to use points+cash (20K+$89) to book a personal stay for the two nights prior. Unfortunately, the property wasn't available at all on Friday evening, so I'm just crashing at an inexpensive Hampton Inn near the airport and then uber'ing to the Diplomat late Saturday morning.
Some questions:- Room selection:I read on TA (and possibly this thread) that it's now possible to choose one's room. Is that via the web? The mobile app? Typically available the day before or day of, right? (not showing anything on the mobile app currently)
- Downside to e-check-in? Sometimes (in general) I've found that front desk people are super-nice and will give me a moderate upgrade; would doing e-check-in reduce the possibility of an in-person upgrade?
- Auto-upgrade? What auto-upgrade, if any, should I expect as a Gold? Or should I just bite the bullet and spend the extra (eStandby) $34/night for an Oceanfront room?

- Keep same room? Lastly, if I do pay for that upgrade, am I near certain to be able to just stay in that same room for both segments (points+cash, subsequent cash stay), since then both would be "1 king bed ocean-front balcony deluxe rooms"?
For reference:- For the points+cash stay Sat-Mon, I currently have reserved "1 king bed intercoastal way superior room"
- For the all-cash stay Mon-Thu, I have "1 king bed ocean-front balcony deluxe room"
- I have Gold status w/ Hilton.
- I'm staying by myself for both segments (not sure if that makes any difference
).
- Forecast: rain :\ (so I suppose I could be spending more time in the room).
Thanks in advance for any of your wisdom!
Updated to add...
Decided to give Reservations a call and just be straightforward and ask re aligning the room types. What I learned:
- Apparently they don't offer the ocean-front rooms on points or points-and-cash stays. Odd.
- She's not able to upgrade me at the moment, either from my status, or even with an upgrade fee.
- She suggested that I avoid checking in early on the phone, and instead wait to speak with a front desk person when I arrive and see if an upgrade (based on status) is possible then.