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It may be the tape(s) themselves. Pre-recorded cassette tapes are usually no problem for most players, but many user-recorded tapes were of the C90 or C120 variety. These cassettes use much thinner tape in order to get the recording time. This can cause the tape, after many starts and stops and partial fast-forwards and rewinds to get tight on the reels. This will cause the tape sensor to think that the tape is at the end of the reel when it is not. Sometimes rewinding from end-to-end will help, but not always,
The unit need some work by a technician. The bad thing about the drawer type decks is that it makes it hard or impossible to clean the tape path. I have not seen one of these but I could probably fix it. Some of your description sound like a loose capstan belt and then other times the Pinch roller is not engaging- they may be related if the mechanism is tied to the capstan motor system.
Insert a blank CD-R or CD-RW into the unit. Press the Function button on the remote (key above Vol+ on the bottom right of the remote) or the turntable itself (top left of the control panel) until the unit is in Phono mode. Then insert the pre-recorded cassette and press Play to advance the tape to where you wish to start recording. With the cassette playing, press the CD Record button (recording will flash on the display). The CD Record button is to the left of the fast reverse button on the unit; it is labeled Record on the remote and is below the Stop button. When one side of the cassette finishes playing, press Stop. Wait for the display to return to Phono. Then eject and turn over the cassette to play side 2 (if you want to record both sides of the tape). Press Play again to advance the tape and then press Record. When this side finishes, press Stop and then Finalize. Finalize is at the bottom left of the remote buttons and to the left of the stand by indicator on the turntable.
the tascam 414 is a 4 track recording studio which uses standard cassette tapes- meaning they only play in one direction, because the tape is full. The 414 records at double speed so that recording fidelity is increased. When you have made a recording you want to mix you then dub your recording though the outputs into another standard tape recorder or whatever you have available, be it a cd recorder or your PC. So, when you listened to your recording on a standard tape player, you were not only hearing it at half speed but you were only listening to 2 of the 4 tracks. The other tracks would only be heard if you flipped the tape over, and they would be heard running backward. I would have though the 414 had a swich to allow it to also record at standard speed to but I guest it does not.