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Thank you for your post!
From FileMaker 5, the files will need to be converted into FileMaker Pro 11 and then into FileMaker Pro 15 or 16. For information and the FileMaker Pro 11 trial see Converting older FileMaker Pro files to the .fmp12 file format. You can receive a Trial of FileMaker Pro 16 by clicking here.
I'm also going to move this thread from the FileMaker Community Feedback Space (which is specifically for input on the Community itself) to the Discussions Space where you should receive more views and potentially more feedback on this topic!
If you have the abilty to open these elderly files before conversion, you might remove all passwords from them These older files do not have accounts like current versions do plus passwords were not case sensitive then, but they are now. This sometimes results in a file that is difficult to open after conversion so it can be best to remove the passwords and recreate your security settings after the fact.
Also be aware that the very structure of how you might set up a solution in FileMaker is much different plus you have many user interface options not possible in the originals. You have both the problem of testing your converted files to see if they work with out additional adjustment and the opportunity to make them far better than the originals.
FileMaker Advanced and good developer support utility such as Base Elements, Inspector Pro, etc could save you many hours of working with the converted files to iron out conversion glitches and to start on the process of improving on them.
Note also that the external data source references in fileMaker 5 files (which were not then accessible to the developer), could easily prove to be very messy with lots of duplication once you convert and check them using FileMaker 15. This doesn't mean that they won't work, but they may be inefficient and can be a challenge to work with until you spend some time cleaning them up--which again is something best done with Filemaker Advanced.
Given the vast changes from 5 to 15, you may find it much easier to just rebuild in FM15 rather than going through the conversion and then trying to fix post-conversion.
It'll depend on number of files, time available, etc.