Swithfire is what Humminbird units have that gives you two ways to control sonar sensitivity. Swithfire CLEAR is mostly automatic, Switchfire MAX is just manual.
For the Humminbird Helix 7 models, ONLY the Helix 7 CHIRP SI GPS G2N model will connect to the Humminbird 360 transducer. That transducer is an Ethernet accessory. BUT you don't need a Side Imaging unit to run the 360. That can be displayed on a Sonar model or Down Imaging model and can provide Side Imaging to those models IF they are the G2N versions.
360 is Side Imaging that rotates.
CHIRP is multi-frequency band sonar. Instead of a single frequency for each sonar pulse, there is a range of frequencies for each pulse. Example is 200 kHz for 2D sonar or in the same band a multi-frequency of 175-225 kHz CHIRP. CHIRP gives better target separation.
All units and brands that have the side looking imaging technology have GPS/mapping.
DragonFly is a Raymarine model with the imaging technoloy copied from Humminbird.
In your price range for Humminbird that can support 360 and has Side Imaging, that would be the Helix 7 CHIRP SI GPS G2N model. The bow 360 version is $1,000 MSRP extra.
The Humminbird Helix models replaced all the units that have number names like the 598ci HD SI Combo. That model was discontinued about 4 years ago.