It depends on what you want to do with it. Two way radio technology is actually fairly simple. The basic mechanics of a radio don’t really change much from unit to unit, or from manufacturer to manufacturer.
Some radios may have flashier features (which you can decide for yourself if you really need) and others might have extra functions, such as the ability to switch between analogue and digital, but, to a large extent, a two way radio is a two-way radio.
A few of the features advertised (and no doubt added to the overall price) will do you no good whatsoever. For example, a radio claiming to have a range of 25-30 miles is simply lying to you. The average radio has a range of between 1 and 2 miles. Some are a little stronger that this, most are not.
Some radios advertise being waterproof or water resistant (some even come with built-in weather warnings) and, if you’re planning on using the radio in more outdoor conditions, then this is definitely a plus and worth spending money on.
Now, as for the tech itself, your radio’s power output is an important factor, but if you are only having a bit of fun, you likely wouldn’t need to go over 0.5 watts (and thus end up applying to Ofcom for a radio license). Generally, FRS (Family Radio Service) radios are cheapest and they are fine for a bit of fun, but GMRS (General Mobile Radio Service) radios, although they cost a little extra, are worth it if you need to transmit a stronger signal over a longer distance.
Other features, such as a built-in LED torch, a stopwatch, built-in alarms and/or a fancy light-up screen are only worth spending out on if you have a use in mind for them. Otherwise, it might be cheaper to simply provide torches and stopwatches to your staff if they require them. That’s a judgment call.
An emergency button, however, is always a good idea. The same is true for a ‘privacy’ function, especially if you are using your radio in an area with lots of other radio signals bouncing about.
Finally, we come to the idea of brand name. Certain products (we could name a particular headphone brand endorsed by a certain rapper, but we won’t) are all about selling the ‘in thing’ with a flashy logo, a branded image, a HUGE markup and little else to offer the customer. Radios are not this way, if you buy a trusted brand (such as Motorola), you can be assured of getting a quality product. In this instance, spending a little more for an established name can definitely pay off.
Essentially, if you want a two-way radio for business use, then it is worth spending out that little extra. However, if you only want one for hobby use, then you can pick one from the lower end of the market and not worry too much about it. Extra features are what add to the price more than anything else and it is entirely up to you to decide if you need them or not.