Here's a subset of your octoprint.log for anything containing "analysis":
2020-04-01 03:17:15,274 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-01 03:17:15,286 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-01 04:20:25,233 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-01 04:20:25,238 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-01 04:20:25,184 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-01 04:20:25,189 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-01 04:20:25,238 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-01 04:20:25,244 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-01 04:59:06,344 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-01 04:59:06,347 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-01 05:17:35,556 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-01 05:17:35,564 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 01:17:13,916 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-02 01:17:13,919 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 01:37:14,172 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-02 01:37:14,179 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 02:26:22,129 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-02 02:26:22,135 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 03:27:40,881 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-02 03:27:40,890 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 03:30:05,825 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-02 03:30:05,833 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 06:08:06,131 - octoprint.filemanager.analysis - INFO - Starting analysis of local:4grey.gcode
2020-04-02 06:08:06,134 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/4grey.gcode
2020-04-02 06:08:28,691 - octoprint.filemanager.analysis - INFO - Starting analysis of local:4grey.gcode
2020-04-02 06:08:28,700 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/4grey.gcode
2020-04-02 06:08:41,544 - octoprint.filemanager.analysis - INFO - Starting analysis of local:4grey.gcode
2020-04-02 06:08:41,546 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/4grey.gcode
2020-04-02 06:09:09,304 - octoprint.filemanager.analysis - INFO - Starting analysis of local:4grey.gcode
2020-04-02 06:09:09,308 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/4grey.gcode
2020-04-02 06:10:07,212 - octoprint.filemanager.analysis - INFO - Analysis of entry local:4grey.gcode finished, needed 57.91s
2020-04-02 06:26:13,430 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-02 06:26:13,431 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-02 16:09:35,336 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 16:09:35,338 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 16:09:49,977 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.64s
2020-04-02 11:15:10,254 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 11:15:10,259 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 11:15:25,233 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.98s
2020-04-02 11:19:04,524 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 11:19:04,529 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 11:19:19,879 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 15.35s
2020-04-02 11:19:28,067 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 11:19:28,070 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 11:40:49,970 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 11:40:49,975 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 11:41:05,387 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 15.42s
2020-04-02 11:41:06,395 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 11:41:06,403 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 11:41:21,040 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.64s
2020-04-02 11:41:22,047 - octoprint.filemanager.analysis - INFO - Starting analysis of local:1grey.gcode
2020-04-02 11:41:22,051 - octoprint.filemanager.analysis - INFO - Invoking analysis command: /home/pi/oprint/bin/python2 -m octoprint analysis gcode --speed-x=6000 --speed-y=6000 --max-t=10 --throttle=0.0 --throttle-lines=100 /home/pi/.octoprint/uploads/1grey.gcode
2020-04-02 11:41:36,638 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.59s
Each one with "finished" means that it thinks it completed the activity.
2020-04-02 06:10:07,212 - octoprint.filemanager.analysis - INFO - Analysis of entry local:4grey.gcode finished, needed 57.91s
2020-04-02 16:09:49,977 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.64s
2020-04-02 11:15:25,233 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.98s
2020-04-02 11:19:19,879 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 15.35s
2020-04-02 11:41:05,387 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 15.42s
2020-04-02 11:41:21,040 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.64s
2020-04-02 11:41:36,638 - octoprint.filemanager.analysis - INFO - Analysis of entry local:1grey.gcode finished, needed 14.59s
Does your Files side panel widget confirm that you have two files added (perhaps after a page reload)?