Back to OP's original questions:
I have no personal experience in owning a hybrid/electric car. Our neighbor owns a Prius and loves it. I've ridden with him and he is AGRESSIVE in his driving in Honolulu traffic but still gets 45mpg or MORE. Our small Island is the perfect place for a hybrid in that it is essentially one big city with several suburbs. Not so perfect is apartment/condo living when it comes to rechargeable cars. We have a number of free plug-in places at shopping centers, but those won't help much as all electric/plug-in hybrids become more popular. In our case, we simply have no place to plug in - even if we were willing to pay for a plug in station.
So, first questions might be "how will you charge a plug-in?" "Do you have a 'safe' place to put in a charging station (such as a locked garage)?" "How many miles do you drive?" IOW "Can you justify the additional cost of a hybrid?" or "Can you do most of your trips in the all-electric's range?"
Next question I would ask is whether OP wants a hybrid/electric to "save money" or because it is such cool technology. Personally, I think the technology is half the reason to own such a vehicle. I would love to have a hybrid or, better yet, a plug-in, just to "play" with it. I'd keep records of mileage, try to see what drive-cycle gives longest battery life, etc. etc. I could spend hours just enjoying such a vehicle. But if it's just to save money, there may be better ways to do that - see below.
Right now, I think we can safely say that hybrids are a nearly mature technology. Owning one - even a used one - should not be too scary as there are a million of them out there working just fine.
All electrics have been around for quite a while as well, but still are not what I would call "mature" though I guess that's debatable. I personally would be less inclined to own one (vs a hybrid or ICE) except, in my case, Oahu is the perfect place in terms of range. Already mentioned lack of a place to charge one (for me, personally). Other than that, Oahu is small enough that I would be willing to own a Leaf, for instance. Most trips are under 25 miles and a "long" trip is a "day trip" of 80 miles around the Island. Someplace in that distance, I could find a recharging station (Typically limited to one hour - perfect for lunch).
If saving money is the main goal, then OP might consider a used ICE instead. Related elsewhere in these pages, I own three used cars (between here and the mainland). Total cost of purchase was about $20K for all 3. Repairs beyond routine (such as brakes) has been less than $4K for all 3 cars. In 9 years, that's a cost of ownership of less than $1000/year/car. Insurance is less because I have no collision coverage. Some states (not mine) offer lower tags cost for older vehicles (my mainland car costs about $50/year for tags.)
There are a lot of factors that go into purchasing a vehicle. My suggestion to OP would be to prioritize these reasons. Cool technology, cost per mile, fuel costs only, insurance cost, tags cost, yearly cost to own, unexpected repairs (used cars mainly), joy of ownership (my favorite car of the 3 is my land-cruising Buick LeSabre!), the list goes on. Once you decide why you want to own a "different" car than currently, your choices may become clearer.
Hope this treatise has been helpful. As always, it is worth every penny you are paying for it since YMMV.