I have my own office too, with 3 glass walls though lol:)
On the pump side, I think it really depends. I read all the recommendations and bought the double electric £200 Medela, and it only gave me bruises and got as much as 1 oz out of me. I now pump twice at work + before bed and during weekends too, so LOTS of pumping, and really love my simple £20 manual Avent, I'm getting 9 oz in 15 min with it no probs.
Suggest you try the simple one, if you don't like it, you can hire the expensive electrical, and see if it works better for you.
Tessa wasn't keen on the bottle in the beginning, and I had really tough time getting her to learn to take it, she loves it now, so that I actually pump and give her bottle on the weekends instead of nursing, so it will take some time and practice, but you lo will get there. Also, Tessa used to take about 80 ml right away, then refuse it, so I'd walk with her till she burps, and then she took same amount again. She's also very conscious on the tempreture of milk, it has to be almost hot, she wouldn't take the lukewarm. See if any of these might work for you.
It's always tough to leave them at first, but they are really adaptable, so it'll get easier as time passes!