I think you summarized the real question well; is $1k a year worth the extra convenience to you?
Economically I think it's a simple calculation: $1k per year, or compounded over 5 & 10 years (assume 7%) would be $5,750 and ~$14,000, respectively. Certainly not chump change, but not a huge amount either for most people's budgets.
Here's just an observation I've had though - when my SO and I decided to go from 2 cars to 1, we had similar worries. Now that we've gone to 1 car, we've rarely had a time when we've desired two, and overall we find it MORE convenient to only have car to worry about. Neither of us need a car to commute, and it was a surprisingly seamless transition. Since two cars is no longer an option, we just stopped considering making plans where both of us would need to go in opposite directions at the same time.
So... I don't miss having two cars at all. YMMV.