When comparing Password Safe vs LessPass, the Slant community recommends LessPass for most people. In the question“What is the best cross-platform password manager?” LessPass is ranked 12th while Password Safe is ranked 13th.
Ranked in these QuestionsQuestion Ranking
Pro Runs on Linux
Pro Anyone can verify the code since the software is open source
Anyone can review the code.
Password Safe has a portable versiona, PasswordSafe2Go.
There is also PasswordSafe for U3 (still supported, but no longer available).
Pro Completely offline
This does not save or synch with any server; no connection to any external server. There is no central server to hack, no network connection to sniff.
Pro Great user interface on Mac and iOS
Since the passwordSafe is essentially an open standard multiple people can use to develop apps. The http://pwsafe.info/ apps for Mac and iOS are really excellent (paid) management options.
Pro Open source
Pro Really platform-free
Pro Doesn't store passwords
If it's not stored, it can't be stolen.
Con No official browser integration
No browser plugins available.
Con Dated UI
Deterministic password managers have many drawbacks.
Con Cannot store existing secrets
Existing secrets (aka passwords) cannot be stored with deterministic password managers. In order to use LessPass effectively, you will need to change your password on every site.
Con Easily cracked with exposed/compromised master password
Since anyone can use LessPass with the same parameters as you, all they need is your master password (which could be obtained through keylogging or numerous other methods) to gain access to every one of your site passwords.