You probably won't. I have a double electric and a single manual and I use the manual every once in a while and it works fine. I wouldn't really want to use it every day, though...
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I can't really help you...my baby was not a rock star on the boob (I am jealous!) and was a "lazy sucker" which means that I ended up bf'ing like 12-14 times a day and pumping 5-8...and then when he became efficient I went to work and pumped there! I think if you're just looking for a small amount, it wouldn't be so bad!
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If you are not going back to work and are just going to be using the pump to create a stash for the occasional night out a single pump will probably suit you fine. I got a Madela single electric and it worked out great for me, but I'm a SAHM and never had to pump regularly (just pumped enough to keep a stash for date nights and girls nights)...
It definitely depends on how you plan to use it. I had both a double electric and a single hand pump. I used the double electric to pump at work, and the single hand pump for nights out (only a handful -- ok, two). I can't imagine having to use the hand pump for regular pumping. However, it was nice to have for those (two) nights out, where dragging the double electric would have been ridiculous.
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Re: How much will I hate my life...
I have no idea. Right now the plan is just pump often enough to have a small fridge/freezer stash b/c the baby has been a rock star on the boob.
If that changes, I'm thinking I'll invest in a double. But until then...??