In ear - flight + daily use, workout ect

Take the cords over ear and you'll be fine. Phonak is also a good all arounder. The ETs are isolation kings with the triplle flange tips but long term comfort is quite variable by individual. They're also a bit etched.hot on top. They're also tougher to remove to speak etc. Phonaks are easy breezy and pretty good at everything. If you want to do a high effeciency ET I'd rather you try thr HF5. Not quite as revealing but better balanced than the 4p. Same isolation and fit considerations. They were pretty much tuned for the triple flanges and deep insertion.

Absolutely not, olives and etys were literally made for each other and imo improves the sound of ety by increasing bass quantity and slam, which is a huge weakness of etys. Olives paired with either HF5s or ER4 will probably give you the best isolation on the planet from an iem, far greater than with the triple flange or stock foams. if you find the right size of olives, for me it was the medium, you can insert them fairly deeply with no discomfort watsoever. I actually found them more comfortable than the ety sponges or any type of flange. 

I've never tried the HF5, but I have used the hf3 (I left them on the bus one horrible day). They were great and they will be right up the alley for what you're looking for. Right now, I use the Shure SE 215. You might want to check those out. They are really good for travel and working out, though I still have an issue with microphonics, or whatever the word is for the cable making noise while I run.

I recommend the Brainwavz B2 for your purposes.

I was using the Brainwavz B2 on a recent flight (approx 150 seats) with shure olives and the isolation was fine even listening to ballads (I only noticed a little turbulance during the silence between tracks).  Probably not as much isolation as the HF5, but I imagine it wasn't far off.  I do own the Etymotic MC5 and depending upon the tips I use, I get either very comforable with poor sound (shure gray silicon) or very uncomfortable with good sound (shure olives and etymotic triple flange).  Not certain how close the MC5 is in terms of fit compared to the HF5.

Given the fit issues I've had with the Etymotic, I can't imagine the HF5 would work out better then the B2 for exercising.  Plus the the Brainwavz B2 has a cable with very little microphonics.

A little off topic, but can anyone verify for me if the B2s are just a rebranded DBA02s and if they sound identical?

Back on track, OP, if you do get HF5s, they should be worn OVER the ears since that will eliminate microphonics almost 100%; with the ER4s, you are stuck wearing them straight down and like the HF5s when worn in similar fashions, the microphonics are quite horrific. 

westones are very good for gym

i used UM2 for couple of years for gym, bike and jogging - very comfortable, stays in ears and their cable can handle a lot of sweat