You do seem to have a problem with your setup somewhere.
Make a backup. You have the option of resetting the Caching Server, but I think that you would have done it given your experience.
You could do the following to inspect the last couple of lines from the Debug log to see some or more (just replace the 12 with another number to see less):
tail -n 12 /Library/Server/Caching/Logs/Debug.log
In terms of completeness for;
sudo ls -al /Library/Server/Caching/Data
this is what the output (taken from my test setup), should more or less look like:
total 5712
drwxr-x---@ 43 _assetcache _assetcache 1462 May 4 00:54 .
drwxrwxr-x 5 _assetcache _assetcache 170 Feb 4 13:49 ..
drwxr-x--- 3 _assetcache _assetcache 102 Apr 5 21:54 03CED5A2-9F00-44AA-A7A0-510D1DAB3FDC
drwxr-x--- 3 _assetcache _assetcache 102 Apr 19 19:14 08F26B13-9720-44AB-94DE-9A3C06025DFD
drwxr-x--- 3 _assetcache _assetcache 102 Apr 21 19:33 13CF0180-6645-48DE-99C1-D241375918D0
drwxr-x--- 3 _assetcache _assetcache 102 Apr 7 09:58 2500BF48-63B6-4827-BD4B-15F315C132C8
drwxr-x--- 3 _assetcache _assetcache 102 Mar 30 05:47 2BE755AA-5CE1-487B-9EAD-7DC680815CAF
drwxr-x--- 3 _assetcache _assetcache 102 May 3 20:54 2E5145CF-F7A3-4755-ABFC-45CBB5A75129
drwxr-x--- 3 _assetcache _assetcache 102 Mar 29 05:47 36AE9A4F-A1EA-4A55-9CC6-B7614BA745B3
drwxr-x--- 3 _assetcache _assetcache 102 Mar 29 20:16 3CF3C620-1259-4D15-BE4A-8C663658A690
drwxr-x--- 3 _assetcache _assetcache 102 May 3 20:54 3DC81070-7294-46C6-8897-14158DC0AD5B
drwxr-x--- 3 _assetcache _assetcache 102 Apr 20 19:15 54780044-7C00-4A46-A091-F790AA385508
drwxr-x--- 3 _assetcache _assetcache 102 Apr 28 07:21 56CCB1C4-702A-4E14-8E64-28589A3ACDAC
drwxr-x--- 3 _assetcache _assetcache 102 Apr 21 21:13 5D602438-BC6C-4546-9165-566BEB8103AD
drwxr-x--- 3 _assetcache _assetcache 102 Mar 31 21:09 68858974-D5CA-4552-B795-23858F73B07D
drwxr-x--- 3 _assetcache _assetcache 102 Apr 10 09:00 694FA6D7-01D3-4EAE-BB6C-507249D35013
drwxr-x--- 3 _assetcache _assetcache 102 Apr 8 20:26 6A4B071E-DEE0-4ADB-8414-BF245D0E3A4D
drwxr-x--- 3 _assetcache _assetcache 102 Apr 28 19:13 761A003C-23AE-43FF-BA9A-38DCEE843B2A
drwxr-x--- 3 _assetcache _assetcache 102 Apr 8 15:31 7CB38E5B-024E-4CBB-8EEF-EA884ABF6636
drwxr-x--- 3 _assetcache _assetcache 102 Apr 29 02:35 7D0A2092-78D2-4FC4-BAEF-9C5B16E38AAB
drwxr-x--- 3 _assetcache _assetcache 102 Mar 31 06:12 80F62BC4-7677-4BD7-B4B5-39AE4DE37E6D
drwxr-x--- 3 _assetcache _assetcache 102 Apr 5 21:54 832A2617-0550-4177-A7DD-EE758339327D
drwxr-x--- 3 _assetcache _assetcache 102 Mar 29 20:16 86972E74-D6B0-4083-9A55-AFABBDFDEFF7
drwxr-x--- 3 _assetcache _assetcache 102 Apr 24 04:27 91E6FB8D-0E00-43E7-9BAA-9A12B0CD176B
drwxr-x--- 3 _assetcache _assetcache 102 Apr 29 02:35 94E449AB-24A9-4D5D-A026-6BBE496E0BC1
drwxr-x--- 3 _assetcache _assetcache 102 May 4 00:54 9C874587-8618-4922-A4D5-B9274FA958BE
drwxr-x--- 3 _assetcache _assetcache 102 Apr 20 22:25 A96A70C5-0502-4609-B4E5-1A3F3D8CEDD0
-rw-r----- 1 _assetcache _assetcache 28672 Feb 4 13:49 AssetInfo.db
-rw-r--r-- 1 _assetcache _assetcache 32768 May 3 21:15 AssetInfo.db-shm
-rw-r----- 1 _assetcache _assetcache 2859312 May 4 05:35 AssetInfo.db-wal
drwxr-x--- 3 _assetcache _assetcache 102 Apr 7 09:58 B1F8A775-0F0D-43E0-BD54-F1E479BF0A66
drwxr-x--- 3 _assetcache _assetcache 102 Apr 27 21:50 B4DE9526-2027-4D6B-B545-D8DD13C40550
drwxr-x--- 3 _assetcache _assetcache 102 Apr 15 00:41 C345A505-4F12-4DD2-8105-BE083AE7A4C2
drwxr-x--- 3 _assetcache _assetcache 102 Mar 29 20:17 C3A8423D-59F1-4830-8F77-EB9BDEFE2732
drwxr-x--- 3 _assetcache _assetcache 102 Apr 20 19:15 D510969A-0543-439C-B38A-9ACF360247E3
drwxr-x--- 3 _assetcache _assetcache 102 Apr 27 10:04 DF1B167A-2D63-4116-8763-45B1777B0130
drwxr-x--- 3 _assetcache _assetcache 102 Mar 29 05:47 E1A4D4C7-271B-4FBF-B4FD-010EFE2C91CF
drwxr-x--- 3 _assetcache _assetcache 102 Apr 27 21:50 E4447B0C-25FF-43D7-A140-761A7DE93AA6
drwxr-x--- 3 _assetcache _assetcache 102 Mar 31 21:09 E7032931-189A-4097-A24F-559353EF2E82
drwxr-x--- 3 _assetcache _assetcache 102 Apr 19 19:14 EAA013FF-4670-40BD-98D7-70C500272ED8
drwxr-x--- 3 _assetcache _assetcache 102 Apr 2 19:45 F778D1D7-3037-4A18-BDF3-8B9955DC047B
drwxr-x--- 3 _assetcache _assetcache 102 Apr 10 09:00 F8C07D12-819F-4E41-B474-2EA92C4C3BBE
drwxr-x--- 2 _assetcache _assetcache 68 Mar 25 12:16 tmp
Leo