Howdy, and welcome to the Volt forum. I live in the South Bay and have a 25-30 mile/day commute, so my 2015 Gen-1 works out just fine. Based on your daily mileage of 80+ per day, a lease is definitely not the way for you to go, as the best deals are on 10K or maybe 12K annual miles. Buying used is generally a pretty good idea for gassers, but it is an especially good idea for the Volt. This is because they take a HUGE dive in resale price based on MSRP (which absolutely nobody pays) due to the Federal and State tax credits/rebates, as well as fear of obsolescence, fear of the "unknown" (as in "is this reliable technology?"), normal depreciation, etc. A 3-year old Volt is likely to have similar mechanical wear-and-tear as a 1-year old gasser, since the electric motor and regen brakes take the brunt of the expected punishment, and they don't suffer nearly as much from it as a full-time gasoline engine and friction brakes would. So picking up a 2013 Gen-1 Volt is a bargain: $12-$15 grand for what is comparatively a practically new car is a terrific "investment" (in quotes, because everyone knows buying a car is almost never an actual investment - it is a set of expenses that is required to perform a necessary task).
A Gen-1 Volt of that MY should return 35-45 miles on electric, based on regular folks' driving habits. Yours are self-described as aggressive, so maybe 35 miles is your max. If your one-way commute is 40 miles, you should generally be able to cover all but ~5 miles on electric. Then L2 charging at work over a typical 8-hour day will easily get you back a full charge for your evening commute. So, 10 miles/day gassing it, at ~40 miles/gallon is only about $3.00 worth of gas per week. Not bad! Now, a Gen-2 will cover your entire commute on electric (so no gas whatsoever on a typical day), but at a significantly higher up-front cost. Like you mentioned, about $20K for a used 2016, versus significantly lower on a used Gen-1. Speaking of price - the $17K you mentioned is a bit high. You should be able to get a loaded 2013 for $15K or better. Remember that a significant portion of these cars are leased, and 2013 was three years ago (the typical lease term). So there is a huge number of recent off-lease, pristine, ultra-low mileage Gen-1 Volts on the market. This, of course, when coupled with dirt-cheap leases on new Volts, as well as the upcoming Bolt release, should keep a lid on used Gen-1 prices. I've seen non-leased 2013 Volts in the $12K area, but that was with 60-70K miles.
My advice for what little it's worth: get a better deal on a used Gen-1 (like $12K-ish). Pay as much cash as you can, and get 3% financing on the balance for as short a term as you can manage. Assuming you can manage $6K cash, the balance of $6K, plus $1K taxes/reg, at 3% interest for 24 months will get you that Volt for around your $300/month limit. Best of luck to you - let us know how it works out!
And yes - those HOV stickers are AWESOME, especially on San Tomas Expressway and 101 :^)
