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Hello again Ray,
I just reread your post and I realized that I didn’t address all you questions.
Regarding the program source, there are two levels to consider. One is what is called “line level”. This is what you get out of a CD player or computer or stereo line output system. The other is a “mic level” which is what comes out of a microphone. All the transmitters I know of use the line level which is much more voltage than a mic level. So, if you need to use a microphone, you will need a microphone preamplifier to convert the mic level to the line level. Many folks use a mixer which accepts both signals and sends the output at line level to a transmitter.
You are correct that the usual FM part15 range is about 200 feet, but car radios are very sensitive. I have a part 15 FM transmitter and using a 19 inch antenna in my basement, I can hear my signal about .2 miles distant.
I am afraid that the only way that you are going to know what range you can get is by trying it. Some claim more than I and some claim less.
If what I wrote sounds complicated, that is because it is, but it can be done. Once you get your program to the line level, transmitting it is easy.