We can fly out of Calgary, My wife just flew from Calgary to Ethiopia in October. It was cheaper, and took around 25 hours to get there and 32 hours coming home. Not great, but not terrible. We have never done a live aboard but my wife isn't sure she wants to be on a vacation where there is nothing other than diving. We like to go out to good restaurants and sight see and that isn't an option on the boats unfortunately. I would definitely do it, but probably not my wife.
This was my first liveaboard, and those were my fears as well.
I didn't notice how long you said you wanted to go for. Depending on your level of adventure-tolerance, Egypt is *so* affordable, you could *easily* (financially) go for two weeks, and have one week of diving and one week of sightseeing. I was there for most of 11 days, but I made a mistake: I had 2 days before and 2 days after the liveaboard. It would have been better to block them together more, and maybe add a couple of days! (The flights dictated the timing: adding those 3 days would have added like $500 to the flight.) I paid $14 a day for lodging and breakfast. Dinner would have been an additional $3, but I wanted to eat out at different places. The room was a 2-bedroom *suite* with wet bar and a bit of balcony and marble everywhere and perfectly clean: but dimly lit and 40 *years* out of date, 4 blocks down a dirt (sand) road, with a half-finished strip mall thingy next door. I ate everything they had for breakfast and felt fine the entire time. But unless you're Eastern European or Russian, the breakfast buffet would *not* be recognizable. I loved it all -- but was OK with adventure.
However, from my experience, Egypt (specifically Hurghada, where I was) would not be a place to go if "good restaurants" (meaning, say 2-3 star level refinement) is a requirement. I really enjoyed it, but two things: 1) I was in the older portion of the city (where the marina is), and I focused on local restaurants and street food, which was uniformly great. The fanciest place I went was
a restaurant named Starfish for wonderful seafood: I ate plenty of great seafood for 300LE ($15 USD). But nothing that I saw pretty much *ANYWHERE* in the city would be what I as a suburban American would consider refined.
If 'dive during the morning, relax in the afternoon, be pampered in the evening' is what you're going for, I would not recommend Hurghada -- or a liveaboard, for that matter. As my wife and I say, there are adventurous vacations, and there are relaxing vacations. Hurghada is an adventurous vacation. Maybe a place like Sharm el Sheikh would be more relaxing? But I doubt it: I don't think any place in the Middle East is going to be relaxing -- certainly not for an American who's never left North America...
And as for liveaboards: there may be ones (way outside of my budget) that have "good restaurant" food, but I'm skeptical. I've been on cruises where people rave about the food, but I disagree. And liveaboards are usually below cruise ships in food quality. After all, how much can you do in a kitchen the size of a closet and a pantry the size of a dorm-room refrigerator? On the one I was on (Emperor Superior), I was pleasantly surprised with the food -- once again, if you get over the fact that you're in a Muslim country (no pork) that caters to Europeans. Enjoyable. But not comfortable.
Sounds like I'm trying to talk you out of it -- especially when everyone else is already giving you great Caribbean options. I would recommend Hurghada to anyone -- as long as they were up for adventure. Seeing as you mentioned Egypt and seemed to eliminate it for logistical reasons that could be addressed, I recommended it. But know what you're getting into!
