Should I be buying a 2nd Gen Prius?

first and foremost, you want good ownership, maintenance and accident records.

how many years would you like to keep it and how many miles per year?

the best way to judge price is relative to every other car you find for sale. you can check kbb.com for help

will you doing maintenance and repairs yourself, or taking it to a good hybrid shop or to a dealer?

do you have a few thousand on hand for unexpected repairs?

 

That's a great price for 2008... Hit me up if you need help doing maintenance once you get a gen2 Prius... I'll be down in your area tending to elderly parents in coming weeks.

 

click on my avatar and then 'start a conversation'

 

there is no way to know how long the battery will last, but from observing here, a goodly percentage make it between 150 and 200k.
you're in cali, so you get the 10/150 warranty

some that are older with lower miles fail because time and not being used is actually bad for them.

the minimum you would have to spend for a new one diy is $1,600. or around 2k installed.

you can option for a refurb like green bean, but experiences vary.

if you can't find a good one with what you can afford, you might be better off with a small gasser like corolla, civic, yaris, mx3, fit, etc.

 

With 240K on original hybrid battery and never an error or failure, as well as having worked on almost 10 hybrid packs I suspect they last longer if they're:

1) driven daily / usually but not always means higher mileage on vehicle
2) cooling fan doesn't get dirty and car lives in a cooler climate with lighter rather than darker paint
3) periodic battery reconditioning & charge/balance once capacity loss is significant (rapid fluctuation of charge levels)
4) corrosion cleaned and inspected regularly

And once the battery does go bad:
1) bad modules replaced before they heat up the rest of the pack and cause damage
2) next modules to fail are found and replaced before they fail
3) periodic reconditioning, charge and balancing

 

@NinjaProdigy unless you're planning to do all the work on the Prius yourself, you might want to take a short trip up to Loscious Garage in San Fran and take a look around and see what their mechanic(s) have to say about your plan.
Hybrid Repair Specialists - Prius Repair - San Francisco - Luscious Garage