You will have a great trip!
Here's my 2 cents!
1-What is the pool situation like at the end of Feb?
CALL the Flamingo and ask if it's open in Feb, many pools close for a few months in the winter for maintenance. If you are hanging your hat there to use the pool, find out from them if it will be open during your dates).
FWIW, it gets downright chilly in Vegas in the winter with snow in the higher elevations of the mountains nearby (not Calgary cold, but hardly sunning/swimming weather). It can be very rainy. I got lucky in early March of 05. It poured and flooded most of Feb, but was sunny and got up to 80 when I was there (first week of March). The pool at the Mirage was open and we had a great time.
2-Any good deals towards the end of Feb?
Yes, if you go after President's Day or before Nascar and March Madness you can find a good deal. If you cna be flexiable, that will work in your favor as far as room rates go. Sign up at the hotels websites (all that strike your fancy) for e-mail promos. Look at the LV convention calendar to see if any major events are happening--they can affect room rates at participating hotels. For example, the Flaming may be $150 per night (waaay too much for the Flamingo), but TI may be $79 (a much better property).
3-Should we book now and risk finding a better deal later?
Depends on how flexiable you are with your dates. If you only have 5 specific dates you can be gone then risking not being able to afford to go isn't worth it (to me, of course). Are you booking air and hotel seperate? If so and your dates are locked, buy your air now if it's a fair price and roll the dice with the room rate (but check the dates against events in Vegas). Don't pay too much to stay at the Flamingo...compare it to Monte Carlo (also has a great pool, with better food, better rooms and a better casino. And a monorail to Bellagio to get you mid strip for free).
4-What's the deal with airport check-in?
Some hotel groups offer a desk where you can check in and have keys issued. I HIGHLY reccommend this for the Flamingo as the lobby check in can be nightmarish (we had an hour wait!).
5-Is there an airport shuttle?
Not a Flamingo run shuttle, but there are companies that offer shuttle service to/from airport/hotels. How many of you are traveling? If it's more than one, take a taxi. From the airport to the Flamingo it might be $15 with tip--simply ask the cabbie for a ballpark before you get in. It's kind of a drag having to make stops on the shuttle only to have a few bucks. On the up side, you get to see a little more than a cab will show you. Cabs go directly there, shuttles most likely will take you to other hotels first.
6-Any rooms better than the others?
I can't help you with this one too much. There is a concierege level, but I have heard the rooms (not suites) are identical, and very generic in my experience.
Tell me how much I'm going to love this hotel (mainly because we can't afford to stay anywhere else with a nice pool!)
I'll give you my honest opinion of the Flamingo. We stayed there only once, and while not a miserable place, it really could be any big resort in any big city. Rooms are tidy, but rather plain. The service is bad (from waiters to front desk to security to dealers--people have worked here a long time and are sort of 'stuck in a rut'), the food is mediocre. The pool and grounds are really very pretty, but I was there in summer and it was so packed with hot sweaty people I couldn't bring myself to even look for a lounge. The location is fantastic.
Veags is about the experience, and I compare what I could get for my money at the Flamingo with comprable priced hotels. Flamingo attracts a lot of retiree snowbirds. If you are that demographic, then you'd be quite comfortable. It's not nearly as flashy or themed or pretty as almost every other big property on the strip.
If you have a super low rate ($50 night) and everything else is twice that, or all you have is $50 then it's great. A clean place to sleep, a great location and a nice pool should the weather cooperate. But compare your rate to the rates of the others hotels on the strip. Look at rates on Lasvegas.com and vegas.com They will give you a good idea of what the hotels have to ofer as far as rates.
FWIW, I did a quick search for Feb 22, 4 nights, 2 people and got an average rate of $135.59 at Flamingo and $149.56 at Monte Carlo. I'd jump on the Monte Carlo rate for the few dollars more.