You can get good headsets regardless of the radio. You just need to match the pins. (They are specific to the brand and the model.) There is a huge variety of headsets for two-way radios available. Check out our forum host’s website.
For your purposes, you may want to consider the “surveillance” style headset. They come with an earpiece that goes in your ear, a curly plastic audio tube behind the ear and a separate mic you clip to your short or collar. The reason why I think these would work best is because you can wear them underneath monitor headphones. I personally like the 1.5 wire headset because there is one wire from the radio to the mic, and a second wire goes to the headset. Others like the 2-wire because they can dangle the mic out the front of their shirt or jacket.
The best advice on headsets, based on wearing them 12-hours for the past 25-years, is to not buy cheap. Get good quality headsets, and especially ones where you can get replacement parts. The clear plastic audio tubes get brittle after a few years, and once you get the tiniest microscopic crack, they need replacing.
If you get the surveillance headsets with the clear plastic audio tube and the plug that goes in your ear, throw the plug away and replace them with ear moulds. Instead of blocking all sounds like the plug, the ear moulds fit inside your ear but doesn’t block out ambient sound. You can still hear clearly through your headphones. They come in three sizes, and most males are medium and most females are small.
As far as radios, you have three choices: rent radios as required for each project; get your own FCC licence, a dedicated frequency and buy your own business radios; or get licence-free radios.
Renting as needed is what film productions do. They get a dedicated frequency and don’t need to worry about licencing, maintenance, programming or extra batteries. Not cheap, but makes the most sense for large productions.
Buying your own business radios is expensive and may be necessary only if you use them a LOT. You get your own dedicated frequency, but budget for the frequency licence, radios, headsets, spare batteries plus time to program and maintain them.
In the licence-free category, you can buy consumer-grade FRS radios that use 22 shared FRS frequencies. Not great for steady use, they are ideal for occasional family use. Made for short-range communication up to a few hundred yards at best in real world conditions, businesses who use them end up replacing them on a regular basis. Consider them throw-away radios when batteries stop charging, headset sockets break or when buttons and switches stop making good contact. Every kid and drive-through in a two mile radius can potentially interfere with your communications, which is why they have 22 channels. Some areas in North America are near-silent on most channels but get near busy places like malls or theme parks and it is hard to find a free frequency.
Most business and FRS radios come with “privacy” or PL-tones (CTCSS/DCS tones) but these do not add frequencies; they prevent your users from hearing transmissions from others unless they broadcast the same PL tone as the ones programmed into your radios. But if someone is broadcasting on the same channel within range of yours, you can still interfere with each other regardless of the “privacy” tones.
The ultimate in licence-free radios in North America are the Motorola DTR and DLR digital radios on the 900 MHz band. They are top quality business-class, military-grade digital radios that use a unique channel-hopping algorithm and cannot be monitored or interfered with by anyone else unless they also have a DTR/DLR radio using the same ID code and channel. (With hundreds of thousands of possibilities, that is not likely.)
They are expensive but have longer range than any VHF or UHF business-class radio in real world conditions, especially inside buildings or structures. Being digital, they are always 100% readable within range.
Because they are digital, they transmit a short “handshake” signal to make sure another radio is within range, and this means there is a slight delay in the transmission. They are not ideal if you need instant communication such as calling cues or safety stops in theatres, but work very well if you can live with the slight (half-second or so) delay.
All radios within the new DTR or DLR family are identical; the only difference is the number of channels one can program.
The difference between the DTR and DLR is that the DTR radios like the existing DTR550 and the new DTR600 and DTR700, can call up individual radios. Other users can still use the same channel even while a private conversation is going.
The DLR radios are more compact, have a built-in antennas and can’t call up individual radios but they can reply privately. Even with the more compact antenna, they have almost as good range as the DTR radios with their longer antennas.
The DLR1020 has two channels and the DLR1060 have six channels (that can be expanded up to ten channels with the latest free customer programming software just released this week from Motorola.) The larger DTR600 has 30 channels and the DTR700 has 50 channels.
If you can afford the cost and can live with the very slight delay in transmissions, I think the Motorola DLR1060 would be ideal for your purposes.