I'm not an expert, but since nobody else has advice, I'll give it a try as I see multiple problems.
#1-"adding the insert...." is likely because you are trying to insert a Mono-Stereo plugin above a Mono plugin. Remove any Mono plugins, or insert the Mono-Stereo plugin last.
#2-"DAE can't get audio...", this could be a few things. How full is your recording hard drive? A recording drive needs to be fast enough(7200 rpm or an SSD) and should have at least 20% free space. Is it a separate drive from C
system drive)? Recording to the C: drive or a partition of the same drive is a bad idea. Are your sessions all backed up to another drive?(they need to be backed up anyway, but this might be a sign of a drive that is beginning to fail). Since you are running PT7.4, I assume everything in your computer is fairly old, so a backup plan is something you NEED TO DO, RIGHT NOW
#3-"Logout has timed out..." can't help without system details
#4-"Cannot audition region..." Not sure, but this could be a setting in IO