Border and S Waugh had to play against the Windies at their peak and didnt have much opportunity to paste rubbish attacks from 2nd rate teams.
In relation to Waugh, I'm not sure I agree.
If you look through the Windies teams Waugh came up against, I believe they broadly fall into three roughly equal periods;
1) Early on in his career against great sides with four brilliant bowlers or 3 brilliant and one competent bowler (typically the likes of Ambrose, Marshall, Walsh and Patterson/Bishop).
2) Mid period - two great (but ageing) bowlers and two fairly ordinary first change bowlers (typically Amrose, Walsh and the Benjamins - Kenny and Winston with the occasional cameo by the injury plagued Bishop)
3) Late career - a very pedestrian attack (typcially Pedro Collins, Mervyn Dhillon, Vasbert Drakes and so on - and, in the 1997-99 period Walsh who by then was bowling in the mid 120's).
In general terms, Waugh's performances against the Windies improved as his career went on for a final average of 49 against the Windies. His early career against a full Windies line up certainly included some brave knocks but was hardly stellar. He came into his own during the second period described above as he peaked and the Windies began their decline.
My point is, the majority of Waugh's test career was not played against the Windies at their peak.
I agree with you regarding Border and, for those reasons, I think it also reinforces how good Greg Chappell was too. Apart from one miserable series (81/82) he had a brilliant record against the Windies at a time when they were at their most ferocious and when protective clothing was still fairly antiquated. For the first half of his career he faced up without a helmet too.