Once you have made up your mind do you need multiple flashes, then the rest is quite easy.
If you shoot alone, its pretty rare that you will use more than one flash. You may use more than one flash in your studio for portrait or group shots, but you can hardly carry two flashes outside alone. To use multiple flashes outdoor, you do need some light stands, and most likely a person who can hold a flash or a reflector for you.
If you have a studio, however, or a place/room where you can setup your lights, then it's great to have multiple flashes.
- Look at the photos you take, how much time you spent on setting up the shot?
If you shoot with a model, its fine to spend some time setting up the shots. In other situations, you may not want to ask your friends and family stand still for 2 minutes while you set up the flashes and everything.
If you prefer working quickly instead of doing "setup shots" , then you will need a TTL flash. Wireless function is also a good choice since off camera flash is invaluable. Or you can get a flash cable.
Maximum power (GN, or guide number) and recycling time are important too.
Having a high GN gives ease of working in sunlight, and in a bigger rooms. If you have a weak flash, you may not be able to light the entire room for wide angle shots. If the ceiling is very high, you may not be able to bounce light off it, too.
Recycling time means how fast can the flash fires in succession. If there is any subject that you only get to shoot once in a dim environment, recycling time becomes extremely important. For photographers shooting fashion show, or celebrity, they must use a flash that allows them to shoot 10 fps. They would go so far to say that "I'd prefer burning the flash then missing a shot" when complaining that they cannot turn off the overheat protection function and shoot until the flash got smoked.
You may not be shooting celebrities but if you want to shoot something in a dark environment and you do not want to miss a shot, consider getting a flash with a fast recycling time.
Cheap manual flashes are good when you:
- want to do static shots at home/studio, like macro or close ups
- have the option to retake the shot in case of failure
In fact, some are so cheap ($25) that I just bought one as tool I can use at home when I do some macro.