Eventually new hardware without legacy drivers can become an issue, XP will go non-support and security fixes won't be released, and new software you require will not support old-time Windows.
While these are not critical issues in the short term, the longer you wait the "behinder" you get.
The biggest changes actually came with Vista, Windows 7 being a relatively modest update akin to XP's SP2. While Microsoft's "XP Mode" has probably given them some incentive to keep XP SP3 on life support XP's end will come. Windows 8 is just around the next corner and it may well be a bigger change again.
There is a tendency to focus on deployment and administration, but foot dragging also makes it tougher to upgrade in-house and custom written applications. Reimplementation costs are wildly under estimated in most organizations, many such projects failing on a regular basis. Vendors working in that space don't help matters either, typically making unrealistic claims.
The cost of rewriting VB6, Delphi, FoxPro, etc. in .Net languages is a good case in point. Few organizations have transitioned their application suites, and where they have hybridized monsters with high support costs can result. Tools are only part of the equation, since the new-OS game changes exist no matter what your software was written in. Remediation of the existing code might have a better payback. .Net is hardly lean or versatile.
Even using legacy development tools targeting Windows XP means sacrificing things that either did not exist until Vista or must be deployed as optional updates to work on XP.
16-bit code is fully supported by Windows 7: on 32-bit Windows 7. If you need it you do have the option. Will you have that choice in Windows 8?
The sands of time are running out and this is very late in the game to be postponing the transition off XP. "We've been sitting on our laurels for 10 years" isn't much of an excuse. Vista and UAC have been a fact of life for almost 5 years now and Windows 7 changed few of the issues.
So I think it is really a question of how long you can wait while the hole you are in gets deeper.