Have you Shut down your computer recently? If not turn it off, wait 2-3 minutes then turn it back on. That can often correct anomalies. I mention this since there is the possibility that the video card or driver being sluggish (possibly it's Cache is full and taking longer to respond or hanging).
When was the last time you ran the RM File > Database tools on these two RM files. If not recently, then do that first after restarting the computer, then try the File > Compare Files again*.
Regarding the two Doreen Person Records: Although they appear to be matches to the human eye (with the exception that one has Glen and the other has Glenn as child, one has Marriage Fact, and other family members not all there in one file), one or both RM files might have a space somewhere in a Vital Fact (Name, Date, or Place, & PLace details) that is not readily visible. Correct so that both files have the same Primary name spelling for Glen/n. Double check both RM files to rule the spaces or other variations out.
Regarding William Smith showing up on right side RM file twice. The match Algorithm might have him twice if he has a spouse or Child that is not showing him as a connection. That '0' match record could also be a 'Ghost' record or a no name record, possibly one that was blanked out, that matches connections to his surrounding family. Check all surrounding family members in both RM files to see if there is one of those type of connections. Otherwise the File > Database Tools should eliminate the 'Ghost' record possibility.
If all else fails, then move each of Doreen's record to the other RM file, then Merge them into the same Person Record. That is if Tim RM file is moved to the Tim-Web-2017... RM file and the opposite is also done, then merge the now 'duplicates into the the Tim-Web-2017... record version, one being the original, the other being the one Time-Web-2017.. record which was moved into the Tim RM file. After this type of merge, they should show up on both sides.
Another thing to note on File > Compare Files is that the Match algorithm typically only produces near exact matches with regard to Vitals, so a Birth entry in one RM file of 'abt 1845' may not match the other RM file with '13 Sep 1845'; even if all else in the record is the same. A period after Jr., Sr. or Dr. can also cause a no match if the other RM file does not have the same. Same situation for any portion of Primary Name and Vital Fact's Date, PLace, & Place Details.
*For 'best practices', the various 'clean-up' features in RM should be utilized before attempting to do any sort of Matching between two RM files. Those features are:
DataClean > PeopleClean - allows you to correct name spelling, punctuations and or other slight differences that might not allow a Match.
DataClean > PlaceClean - allows you to correct name spelling, punctuations and or other slight differences that might not allow a Match.
Edit > Place List - look it over for duplicate entries and or is Place List entries are Standardized & GeoCoded as best as possible.
Edit > Source List - merge any duplicates found
Edit > Fact Type List - both files should have the same spelling if any Custom Facts have been created; especially Custom Facts that are very close to, or used in place of, RM standard Vital Facts. Something like Education Fact in one RM file and Graduation Fact in another RM file might be the same data, If one term is used in one and a different in the other RM file, then these will end up as two entries that do not match; or the may also not cause there to be a Match.