I am a house painter by trade. I spend a lot of time on ladders. I ALWAYS prefer to use the smallest/lightest ladder that works for the job. The difference between moving a 24 and 28 footer is very noticeable.
My preference is a Type 1 250lb or Type 1A 300lb Aluminum 24'.
The Type II 225lb ladders are generally too bouncy/noodley in my opinion.
Another thing to consider if you are going to be working on any kind of incline/off kilter terrain adjustable leveling legs like
THESE are absolutely amazing. A lot safer than that stack of 2x4s and rocks that you would be using otherwise!
Also get your self a set of
Werner extension covers as well. They'll keep the ladder from banging up the siding but they also do a lot to help it grip, keeping it from sliding as well.
Go out and measure the tallest side of your house, since you just want it for around the house then there is no reason to go taller than that side of the house.