Hi,
Deleting the .plist linked to the app may help.
These are in your User Folder (the Little House icon) and then Library. ) often written as ~/Library
However this Library is normally invisible.
Open a Finder's Window and use the GO Menu.
At the same time hold the ALT key down.
Select the Library that appears in the Menu list and then Navigate to Preferences.
Delete all the items that Start com.apple.iChat and end in .plist
Also delete com.apple.imagent.
Follow that by also deleting
com.apple.imservice.ids.iMessage.plist
com.apple.imessage.plist
com.apple.imessages.bag.plist
In the Home Folder/Library there is also the Messages folder.
Deleting the three Data bases will remove all records of the iMessages you have had.
It also removes the Summaries of any Saved Chat you may have made in the past.
Those are stored in ~/Library/Containers/com.apple.iChat/Data/Library/Messages/Archive
IN this Messages folder there is also an Alias to the Attachments in the ~/Library/Messages/Attachments (where the database items are)
There are more .plist in ~/Library/Containers/com.apple.soagent/Data/Library/Preferences
Start with com.apple.messageshelper.AccountInfoController.plist and works down the few with messagehelper in the name that are actual files and not Aliases.
Doing all of this is likely to cause Messages to be reset as far as Preferences, some Menu choices that can be made and other peripheral settings, along with the History to the Messages you may have had.
It is unlikely to sort out the issue with the File/Picture Transfers

8:48 pm Wednesday; February 14, 2018
iMac 2.5Ghz i5 2011 (Sierra)
G4/1GhzDual MDD (Leopard 10.5.8)
MacBookPro 2Gb (Snow Leopard 10.6.8)
Mac OS X (10.6.8),
iPhone 6 iOS 11.x and an iPad (2)