If the Arduino is anything like a PIC µC then you have no hope of sampling at 44KHz. Most simple µC have quite a slow sampling rate (like 100's of samples per second).
If you want faster then you'd be looking at using something like a dsPIC which has an actual audio grade ADC in it, or use an audio ADC externally that can send I²S data to a µC that is fast enough to respond to it.
I have done some similar work recently while designing a digitally controlled amp.
I had the output of the first stage of the amp going into an analog input on the controlling PIC to then control a bargraph of LEDs for a simple VU meter.
For an output from a PC soundcard you're probably looking at around 1 to 2 volts voltage swing. For my system I wasn't too fussed about frequency and such - just pure peak amplitude - so I passed the signal through a small shottky diode first to trim off the negative voltages. This simplified my design a whole lot.
I am also designing a small frequency analyzer at the moment, and am looking at having selectable op-amp based band-pass filters based around this design: http://www.wa4dsy.net/robot/bandpass-filter-calc which so far has given quite good results. I am varying some of the resistor values by a combination of digital pots and analog multiplexers.
I would certainly recommend at least protecting your analog input(s) with op-amps to limit the maximum voltage they get - just in case. You don't want a voltage spike blowing up your Arduino now do you? Easier to replace a blown op-amp.
And as for a signal for testing? There are many free signal generators for the PC available for download if you do a little google for them. They will let you select waveform, frequency, amplitude, phase, etc. Even allow summing of waveforms to give new waveforms if you're lucky.
You can even use your PC soundcard as a rudimentary scope as well with the right software and a small home-made probe. There is software and designs around for this too on the net.
Oh, and remember to isolate different stages / voltage levels with capacitors in the audio signal. As a rule of thumb, if I am changing PSU voltage levels, I always introduce a capacitor to isolate the stages. So, I had one on the input signal, one on the stage 1 -> stage 2 (+/-5V to +/-12V power supply), one on the stage 1 -> analog input, and one again on the output. It pays to take no chances with stray DC offsets wandering into the wrong part of the circuit.
Sounds like you should consider placing some good quality capacitors in series with the audio signal lines from the jack that you added and to where you connected the inputs to the guts of the old cassette player's amplifier input. I would start with a value of 10uF with a voltage rating of 16V or more. It would be best to utilize non-polarized capacitors but if you cannot find those then consider one of two options:
a) Use two 22uF capacitors in series wires + to + and then one - lead to the jack and the other - lead to the cassette input.
b) Try to see how a polarized cap would work. Put the + lead toward the cassette player amplifier and the - to the jack.
These capacitor ideas block the DC bias that is apparently present at the connection point where you attached the signal wires into the cassette amplifier board. Some of the earlier devices that you connected to the cassette jack may very well have had capacitor coupled outputs. On the other hand your newest device may not have an output configured like this.
Best Answer
OK now I'm confident to answer this: -
Analogue cable radio doesn't use FM or AM transmission - it uses data from a coax coming into your home.
If you do have analogue radios that work the traditional way you can buy small FM transmitters (intended for iPhone to car radio connections) just like these
You can get cheaper ones that just take an audi input jack too.
If you are still intent on making an FM transmitter (mono for simplicity) here's a link to a design site with several on.