diff --git a/setuptools/msvc.py b/setuptools/msvc.py
index 313a781ae0..698b23d7af 100644
--- a/setuptools/msvc.py
+++ b/setuptools/msvc.py
@@ -17,6 +17,9 @@
 
 from more_itertools import unique_everseen
 
+from ._path import StrPath
+from .compat import py310
+
 import distutils.errors
 
 if TYPE_CHECKING:
@@ -135,7 +138,7 @@ def target_dir(self, hidex86=False, x64=False) -> str:
             else rf'\{self.target_cpu}'
         )
 
-    def cross_dir(self, forcex86=False):
+    def cross_dir(self, forcex86=False) -> str:
         r"""
         Cross platform specific subfolder.
 
@@ -306,7 +309,7 @@ def microsoft(self, key, x86=False):
         node64 = '' if self.pi.current_is_x86() or x86 else 'Wow6432Node'
         return os.path.join('Software', node64, 'Microsoft', key)
 
-    def lookup(self, key, name):
+    def lookup(self, key: str, name: str) -> str | None:
         """
         Look for values in registry in Microsoft software registry.
 
@@ -319,7 +322,7 @@ def lookup(self, key, name):
 
         Return
         ------
-        str
+        str | None
             value
         """
         key_read = winreg.KEY_READ
@@ -366,7 +369,7 @@ class SystemInfo:
     ProgramFiles = environ.get('ProgramFiles', '')
     ProgramFilesx86 = environ.get('ProgramFiles(x86)', ProgramFiles)
 
-    def __init__(self, registry_info, vc_ver=None) -> None:
+    def __init__(self, registry_info: RegistryInfo, vc_ver=None) -> None:
         self.ri = registry_info
         self.pi = self.ri.pi
 
@@ -486,7 +489,7 @@ def _as_float_version(version):
         return float('.'.join(version.split('.')[:2]))
 
     @property
-    def VSInstallDir(self):
+    def VSInstallDir(self) -> str:
         """
         Microsoft Visual Studio directory.
 
@@ -504,7 +507,7 @@ def VSInstallDir(self):
         return self.ri.lookup(self.ri.vs, f'{self.vs_ver:0.1f}') or default
 
     @property
-    def VCInstallDir(self):
+    def VCInstallDir(self) -> str:
         """
         Microsoft Visual C++ directory.
 
@@ -608,7 +611,7 @@ def WindowsSdkLastVersion(self):
         return self._use_last_dir_name(os.path.join(self.WindowsSdkDir, 'lib'))
 
     @property
-    def WindowsSdkDir(self) -> str | None:  # noqa: C901  # is too complex (12)  # FIXME
+    def WindowsSdkDir(self) -> str:  # noqa: C901  # is too complex (12)  # FIXME
         """
         Microsoft Windows SDK directory.
 
@@ -651,13 +654,13 @@ def WindowsSdkDir(self) -> str | None:  # noqa: C901  # is too complex (12)  # F
         return sdkdir
 
     @property
-    def WindowsSDKExecutablePath(self):
+    def WindowsSDKExecutablePath(self) -> str | None:
         """
         Microsoft Windows SDK executable directory.
 
         Return
         ------
-        str
+        str | None
             path
         """
         # Find WinSDK NetFx Tools registry dir name
@@ -688,7 +691,7 @@ def WindowsSDKExecutablePath(self):
         return None
 
     @property
-    def FSharpInstallDir(self):
+    def FSharpInstallDir(self) -> str:
         """
         Microsoft Visual F# directory.
 
@@ -701,13 +704,13 @@ def FSharpInstallDir(self):
         return self.ri.lookup(path, 'productdir') or ''
 
     @property
-    def UniversalCRTSdkDir(self):
+    def UniversalCRTSdkDir(self) -> str | None:
         """
         Microsoft Universal CRT SDK directory.
 
         Return
         ------
-        str
+        str | None
             path
         """
         # Set Kit Roots versions for specified MSVC++ version
@@ -717,12 +720,12 @@ def UniversalCRTSdkDir(self):
         for ver in vers:
             sdkdir = self.ri.lookup(self.ri.windows_kits_roots, f'kitsroot{ver}')
             if sdkdir:
-                return sdkdir or ''
+                return sdkdir
 
         return None
 
     @property
-    def UniversalCRTSdkLastVersion(self):
+    def UniversalCRTSdkLastVersion(self) -> str:
         """
         Microsoft Universal C Runtime SDK last version.
 
@@ -731,7 +734,11 @@ def UniversalCRTSdkLastVersion(self):
         str
             version
         """
-        return self._use_last_dir_name(os.path.join(self.UniversalCRTSdkDir, 'lib'))
+        try:
+            return self._use_last_dir_name(os.path.join(self.UniversalCRTSdkDir, 'lib'))  # type: ignore[arg-type] # Expected TypeError
+        except TypeError as ex:
+            py310.add_note(ex, "Cannot find UniversalCRTSdkDir")
+            raise
 
     @property
     def NetFxSdkVersion(self):
@@ -751,16 +758,16 @@ def NetFxSdkVersion(self):
         )
 
     @property
-    def NetFxSdkDir(self):
+    def NetFxSdkDir(self) -> str | None:
         """
         Microsoft .NET Framework SDK directory.
 
         Return
         ------
-        str
+        str | None
             path
         """
-        sdkdir = ''
+        sdkdir: str | None = ''
         for ver in self.NetFxSdkVersion:
             loc = os.path.join(self.ri.netfx_sdk, ver)
             sdkdir = self.ri.lookup(loc, 'kitsinstallationfolder')
@@ -769,7 +776,7 @@ def NetFxSdkDir(self):
         return sdkdir
 
     @property
-    def FrameworkDir32(self):
+    def FrameworkDir32(self) -> str:
         """
         Microsoft .NET Framework 32bit directory.
 
@@ -785,7 +792,7 @@ def FrameworkDir32(self):
         return self.ri.lookup(self.ri.vc, 'frameworkdir32') or guess_fw
 
     @property
-    def FrameworkDir64(self):
+    def FrameworkDir64(self) -> str:
         """
         Microsoft .NET Framework 64bit directory.
 
@@ -855,13 +862,13 @@ def _find_dot_net_versions(self, bits) -> tuple[str, ...]:
         return ()
 
     @staticmethod
-    def _use_last_dir_name(path, prefix=''):
+    def _use_last_dir_name(path: StrPath, prefix: str = '') -> str:
         """
         Return name of the last dir in path or '' if no dir found.
 
         Parameters
         ----------
-        path: str
+        path: StrPath
             Use dirs in this path
         prefix: str
             Use only dirs starting by this prefix
@@ -877,7 +884,7 @@ def _use_last_dir_name(path, prefix=''):
             if os.path.isdir(os.path.join(path, dir_name))
             and dir_name.startswith(prefix)
         )
-        return next(matching_dirs, None) or ''
+        return next(matching_dirs, '')
 
 
 class _EnvironmentDict(TypedDict):
@@ -1200,7 +1207,7 @@ def _sdk_tools(self):
             yield self.si.WindowsSDKExecutablePath
 
     @property
-    def _sdk_subdir(self):
+    def _sdk_subdir(self) -> str:
         """
         Microsoft Windows SDK version subdir.
 
@@ -1345,7 +1352,7 @@ def HTMLHelpWorkshop(self):
         return [os.path.join(self.si.ProgramFilesx86, 'HTML Help Workshop')]
 
     @property
-    def UCRTLibraries(self):
+    def UCRTLibraries(self) -> list[str]:
         """
         Microsoft Universal C Runtime SDK Libraries.
 
@@ -1358,12 +1365,16 @@ def UCRTLibraries(self):
             return []
 
         arch_subdir = self.pi.target_dir(x64=True)
-        lib = os.path.join(self.si.UniversalCRTSdkDir, 'lib')
+        try:
+            lib = os.path.join(self.si.UniversalCRTSdkDir, 'lib')  # type: ignore[arg-type] # Expected TypeError
+        except TypeError as ex:
+            py310.add_note(ex, "Cannot find UniversalCRTSdkDir")
+            raise
         ucrtver = self._ucrt_subdir
         return [os.path.join(lib, f'{ucrtver}ucrt{arch_subdir}')]
 
     @property
-    def UCRTIncludes(self):
+    def UCRTIncludes(self) -> list[str]:
         """
         Microsoft Universal C Runtime SDK Include.
 
@@ -1375,11 +1386,15 @@ def UCRTIncludes(self):
         if self.vs_ver < 14.0:
             return []
 
-        include = os.path.join(self.si.UniversalCRTSdkDir, 'include')
+        try:
+            include = os.path.join(self.si.UniversalCRTSdkDir, 'include')  # type: ignore[arg-type] # Expected TypeError
+        except TypeError as ex:
+            py310.add_note(ex, "Cannot find UniversalCRTSdkDir")
+            raise
         return [os.path.join(include, f'{self._ucrt_subdir}ucrt')]
 
     @property
-    def _ucrt_subdir(self):
+    def _ucrt_subdir(self) -> str:
         """
         Microsoft Universal C Runtime SDK version subdir.