As others have said, first thing to do is take a refresher course or two, just to update your skills.
Regarding the bike - try and take a decent test ride before buying anything. Small to mid-size cruisers are generally quite uncomfortable for long rides, so make sure it's really what you want. Also, scraping the pegs on every corner gets old pretty fast.
Two things I insist on having on my bikes is EFI and ABS. Nothing wrong with carbs, but as they age, they wear out and need fettling, whereas EFI is pretty well maintenance free. Consistent starting whether hot or cold too. The benefits of ABS are obvious - even more so for a returning rider.
Are you comfortable maintaining a chain? If so, I reckon a V-Strom 650 is the perfect bike for you. Later model ones have ABS. They can cruise at highway speeds all day even with a passenger, have a reasonable amount of wind and weather protection, good fuel range and will do some light off roading. There is loads of aftermarket support too.
Whatever you buy, go for something as standard as possible. Stuff like heated grips, top box, crash bars, a quality aftermarket muffler, etc. are ok, anything beyond that should have alarm bells sounding. Lastly, take a friend who knows bikes to look over any potential purchase with you. Good luck!