This is most definitely an infinity loop (paradox)
Timeline A-B
Joe 1 kills his older self, collects his money, retires, and then enters the time machine as a much older person, destined for the past (point C). For some reason he is fine with dying in the same manner as the Joe he killed, or perhaps is unable to resist.
Timeline C-D
Joe 2 kills his older self and follows the same path as the A-B timeline, the difference here being that he is somehow mentally or physically different, which will allow him to escape in the E-F timeline. He gets captured and is sent back in time (point E).
Timeline E-F
Joe 2 arrives and escapes Joe 3. How it is possible that he is able to escape when the Joe he killed could not escape him is unfortunately a huge plot hole, but let's ignore it for now. The movie happens. Joe 3 kills himself and Joe 2 dies as well. Time progresses to the point where Joe 3 would have grown up and traveled back in time. This does not happen. Since Joe 3 has not traveled back in time, he never was able to escape a potential Joe 4 which leads to the infinity loop. Time snaps back to it's last stable point, which is the A-B timeline.
The A-B timeline somehow moves into the ambiguous C-D timeline where Joe learns the true meaning of life or whatever and knows how to escape his younger self when he is sent back, and then on to the move timeline of E-F, which ends in a paradox which continues the loop back with A-B.
Wash, Rinse, Repeat.