Kawasaki 250 and newer 300 are very upright. They come with regular bars across the top.
They hold their values well on the used market as long as they are well maintained.
Red line on the new ones is 14k, old ones 15k. Fun when wound up.
A neighbor had a 95 900 Monster he got down in Oregon for $2500. He had to have it.
Kind of rustles the jimmies thing and had a lot of fun with it.
It was a carburated bike though and was always having to d1ck around with it.
Turns out the needles had ovalized the emulsion tubes and would never be the same without new carbs.
He finally sold it and got a Multistrada with fuel injection.
Another bike to look at would be a Suzuki SV650. They're going for about the same as a 250/300.
It's a 90 degree L twin that comes as a naked with bars or faired with clipons.
99-02 have carbs, but 03 on are injected. Would recommend injected.
Then you can get your Monster when it's just not enough.
I've got an 03 naked that is going to be another long term bike.
Last one was an 83 Honda Nighthawk 650 that I had for 23 years. Carbs finally.
I like my SV a lot. Good low end torque, perfect for stop n go city traffic. It goes to 11!
It's almost as good as a monster, but a lot cheaper initially and for parts later. Engine braking and blip downshifts. Live it.
You will get best value for a used bike as a private sale, but you have to know what to look for and how much to fix it if it's not right.
A dealer may let you bring it back for 30 days, but don't count on it getting better spontaneously.
Tires over 5 years old definitely need replacing. There are codes on the sidewalls. $300+ for a new set of adequate tires.
A good resource for checking out used SVs was written up, but a lot of it applies to all used bike shopping.
mad8vskillz' SV650 "Good Dealz" Buying Guide