The following is quoted from a guy whose account no longer exists:
hear me out.
2004-2009 Honda Shadow Aero 750.
the bike weighs VERY little, like low 500 lbs. so they are SUPER lightweight, easy to upgrade to from a 250.
the motor has a very good power curve, and even for being a 750, is actually REALLY nice because the bike weighs so little.
in 2004 the shadow was re-designed, and its the SAME bike you can buy today in 2016. the new ones have EFI, but the CV carbs on the 2004-2009 are SO fucking reliable that if you ride it often and never let gas get stale, you may never have a problem. I rode mine daily for 5 years straight and never had to touch the carb. at all.
the shadows have shaft drive (no maintenance), and the light weight means tires and brakes last longer before you need to replace them, so less maintenance there too. They are watercooled and Honda builds bikes to a higher standard than most other brands, you have to do oil changes and valve clearance adjustments, and that should be the only maintenance you have to do besides the big things that come up every few years.
parts availability is great because the 2004+ shadow is STILL in production.
you can go to a dealer, test ride a 2015 shadow aero and know what to expect from the bike, then go to a private sale and buy one for under 3k and know what your getting into riding-wise.
best of all, it is currently the best looking cruiser out of all modern production japanese cruisers. the others have too many angles, sharp lines, exposed hoses and random bits sticking out (looking at you, Bolt...) and the shadow aero just looks ...."right". its got the right shape, the right lines. it looks low and long but actually has a lot of clearance and suspension for its shape.
give it a try. worst you can do is test ride it and its a bad fit for your body type. floorboards and heel-toe shifters on the shadow aero are amazing. I used to ride mine 300-600 miles per day and be totally comfortable like a goldwing.
what you want to avoid when looking for a used one is low mileage. if you are looking at a super low mileage bike, it means it SAT for a long time, which means the carb can get gummed up, the rubber hoses can get cracked, moisture can be inside the engine causing pitting and rust on internal components.
a higher mileage (40-60k) bike usually means the owner 1. took care of it 2. had to service it properly in order to KEEP putting miles on it, and 3. made sure it never sat un-used.
the bikes are good for 200k miles with just brake pads, oil changes, tires, and valve adjustments. you shouldnt ever have to do any serious engine work on them even in extreme mileage scenarios