Leaving the bumping of dependent ports aside, here's what I have
collected so far as the required changes to actually perform the
switch from gcc4.9 to gcc8:

* switch gcc4 module to gcc/8
* register the gcc/8 subpackages as updates for their gcc/4.9 counterparts
* sync the gcc version in devel/llvm
* add a quirk entry that gcj is obsolete
* unhook 4.9 from the build

Anything missing?

Index: devel/llvm/Makefile
===================================================================
RCS file: /cvs/ports/devel/llvm/Makefile,v
retrieving revision 1.216
diff -u -p -r1.216 Makefile
--- devel/llvm/Makefile 9 Mar 2019 06:18:11 -0000       1.216
+++ devel/llvm/Makefile 27 Apr 2019 19:48:43 -0000
@@ -20,7 +20,7 @@ PKGSPEC-main =        llvm-=${LLVM_V}
 PKGNAME-main = llvm-${LLVM_V}
 PKGNAME-python =       py-llvm-${LLVM_V}
 PKGNAME-lldb = lldb-${LLVM_V}
-REVISION-main =        9
+REVISION-main =        10
 REVISION-lldb =        0
 CATEGORIES =   devel
 DISTFILES =    llvm-${LLVM_V}.src${EXTRACT_SUFX} \
@@ -114,7 +114,7 @@ PKG_ARGS +=         -Dpowerpc=0
 TEST_TARGET =          check
 
 # XXX sync
-GCC_VER =              4.9.4
+GCC_VER =              8.3.0
 .if ${MACHINE_ARCH} == "amd64"
 GCC_CONFIG =           x86_64-unknown-openbsd${OSREV}
 .else
Index: devel/quirks/Makefile
===================================================================
RCS file: /cvs/ports/devel/quirks/Makefile,v
retrieving revision 1.737
diff -u -p -r1.737 Makefile
--- devel/quirks/Makefile       26 Apr 2019 15:10:32 -0000      1.737
+++ devel/quirks/Makefile       26 Apr 2019 20:22:39 -0000
@@ -5,7 +5,7 @@ CATEGORIES =    devel databases
 DISTFILES =
 
 # API.rev
-PKGNAME =      quirks-3.130
+PKGNAME =      quirks-3.131
 PKG_ARCH =     *
 MAINTAINER =   Marc Espie <es...@openbsd.org>
 
Index: devel/quirks/files/Quirks.pm
===================================================================
RCS file: /cvs/ports/devel/quirks/files/Quirks.pm,v
retrieving revision 1.754
diff -u -p -r1.754 Quirks.pm
--- devel/quirks/files/Quirks.pm        26 Apr 2019 15:10:32 -0000      1.754
+++ devel/quirks/files/Quirks.pm        26 Apr 2019 20:23:05 -0000
@@ -1215,6 +1215,7 @@ my $obsolete_reason = {
        'py3-async' => 5,
        'py3-funcsigs' => 5,
        'rust-doc' => 1,
+       'gcj' => 5,
 };
 
 # reasons for obsolete packages
Index: infrastructure/mk/gcc4.port.mk
===================================================================
RCS file: /cvs/ports/infrastructure/mk/gcc4.port.mk,v
retrieving revision 1.13
diff -u -p -r1.13 gcc4.port.mk
--- infrastructure/mk/gcc4.port.mk      2 Feb 2019 18:44:38 -0000       1.13
+++ infrastructure/mk/gcc4.port.mk      22 Apr 2019 22:02:38 -0000
@@ -1,6 +1,2 @@
-.if ${MACHINE_ARCH} == "aarch64"
 MODGCC4_VERSION?=8
-.else
-MODGCC4_VERSION?=4.9
-.endif
 .include "${PORTSDIR}/lang/gcc/${MODGCC4_VERSION}/gcc4.port.mk"
Index: lang/gcc/Makefile
===================================================================
RCS file: /cvs/ports/lang/gcc/Makefile,v
retrieving revision 1.16
diff -u -p -r1.16 Makefile
--- lang/gcc/Makefile   2 Feb 2019 18:44:03 -0000       1.16
+++ lang/gcc/Makefile   23 Apr 2019 13:04:32 -0000
@@ -1,7 +1,6 @@
 # $OpenBSD: Makefile,v 1.16 2019/02/02 18:44:03 pascal Exp $
 
      SUBDIR =
-     SUBDIR += 4.9
      SUBDIR += 8
 
 .include <bsd.port.subdir.mk>
Index: lang/gcc/8/Makefile
===================================================================
RCS file: /cvs/ports/lang/gcc/8/Makefile,v
retrieving revision 1.9
diff -u -p -r1.9 Makefile
--- lang/gcc/8/Makefile 25 Mar 2019 20:17:46 -0000      1.9
+++ lang/gcc/8/Makefile 19 Apr 2019 20:13:37 -0000
@@ -11,6 +11,7 @@ ONLY_FOR_ARCHS-ada = amd64 hppa i386 mip
 DPB_PROPERTIES = parallel
 
 V = 8.3.0
+REVISION = 0
 FULL_VERSION = $V
 FULL_PKGVERSION = $V
 
Index: lang/gcc/8/pkg/PLIST-ada
===================================================================
RCS file: /cvs/ports/lang/gcc/8/pkg/PLIST-ada,v
retrieving revision 1.1.1.1
diff -u -p -r1.1.1.1 PLIST-ada
--- lang/gcc/8/pkg/PLIST-ada    4 Jan 2019 15:50:40 -0000       1.1.1.1
+++ lang/gcc/8/pkg/PLIST-ada    19 Apr 2019 20:24:05 -0000
@@ -1,5 +1,7 @@
 @comment $OpenBSD: PLIST-ada,v 1.1.1.1 2019/01/04 15:50:40 pascal Exp $
 @option is-branch
+@conflict gnat-<9
+@pkgpath lang/gcc/4.9,-ada
 @bin bin/gnat
 @bin bin/gnatbind
 @bin bin/gnatchop
Index: lang/gcc/8/pkg/PLIST-c++
===================================================================
RCS file: /cvs/ports/lang/gcc/8/pkg/PLIST-c++,v
retrieving revision 1.1.1.1
diff -u -p -r1.1.1.1 PLIST-c++
--- lang/gcc/8/pkg/PLIST-c++    4 Jan 2019 15:50:40 -0000       1.1.1.1
+++ lang/gcc/8/pkg/PLIST-c++    19 Apr 2019 20:26:02 -0000
@@ -1,6 +1,8 @@
 @comment $OpenBSD: PLIST-c++,v 1.1.1.1 2019/01/04 15:50:40 pascal Exp $
 @option is-branch
 @conflict gcc-libs->=9
+@conflict g++-<9
+@pkgpath lang/gcc/4.9,-c++
 @bin bin/ec++
 @bin bin/eg++
 @bin bin/${CONFIG}-ec++
Index: lang/gcc/8/pkg/PLIST-f95
===================================================================
RCS file: /cvs/ports/lang/gcc/8/pkg/PLIST-f95,v
retrieving revision 1.1.1.1
diff -u -p -r1.1.1.1 PLIST-f95
--- lang/gcc/8/pkg/PLIST-f95    4 Jan 2019 15:50:40 -0000       1.1.1.1
+++ lang/gcc/8/pkg/PLIST-f95    19 Apr 2019 20:27:13 -0000
@@ -2,6 +2,8 @@
 @option is-branch
 @conflict gfortran-*
 @conflict libgfortran-*
+@conflict g95-<9
+@pkgpath lang/gcc/4.9,-f95
 @bin bin/egfortran
 @bin bin/${CONFIG}-egfortran
 @info info/gfortran.info
Index: lang/gcc/8/pkg/PLIST-libs
===================================================================
RCS file: /cvs/ports/lang/gcc/8/pkg/PLIST-libs,v
retrieving revision 1.1.1.1
diff -u -p -r1.1.1.1 PLIST-libs
--- lang/gcc/8/pkg/PLIST-libs   4 Jan 2019 15:50:40 -0000       1.1.1.1
+++ lang/gcc/8/pkg/PLIST-libs   19 Apr 2019 20:27:40 -0000
@@ -1,7 +1,8 @@
 @comment $OpenBSD: PLIST-libs,v 1.1.1.1 2019/01/04 15:50:40 pascal Exp $
 @option no-default-conflict
 @option is-branch
-@conflict gcc-libs->=8,<9
+@conflict gcc-libs-<9
+@pkgpath lang/gcc/4.9,-libs
 lib/libatomic.la
 @lib lib/libatomic.so.${LIBatomic_VERSION}
 lib/libestdc++.la
Index: lang/gcc/8/pkg/PLIST-main
===================================================================
RCS file: /cvs/ports/lang/gcc/8/pkg/PLIST-main,v
retrieving revision 1.1.1.1
diff -u -p -r1.1.1.1 PLIST-main
--- lang/gcc/8/pkg/PLIST-main   4 Jan 2019 15:50:40 -0000       1.1.1.1
+++ lang/gcc/8/pkg/PLIST-main   19 Apr 2019 20:28:05 -0000
@@ -1,5 +1,7 @@
 @comment $OpenBSD: PLIST-main,v 1.1.1.1 2019/01/04 15:50:40 pascal Exp $
 @option is-branch
+@conflict gcc-<9
+@pkgpath lang/gcc/4.9,-main
 @bin bin/ecpp
 @bin bin/egcc
 @bin bin/egcc-ar
Index: lang/gcc/8/pkg/PLIST-objc
===================================================================
RCS file: /cvs/ports/lang/gcc/8/pkg/PLIST-objc,v
retrieving revision 1.1.1.1
diff -u -p -r1.1.1.1 PLIST-objc
--- lang/gcc/8/pkg/PLIST-objc   4 Jan 2019 15:50:40 -0000       1.1.1.1
+++ lang/gcc/8/pkg/PLIST-objc   19 Apr 2019 20:28:50 -0000
@@ -1,5 +1,7 @@
 @comment $OpenBSD: PLIST-objc,v 1.1.1.1 2019/01/04 15:50:40 pascal Exp $
 @option is-branch
+@conflict gobjc-<9
+@pkgpath lang/gcc/4.9,-objc
 lib/gcc/${CONFIG}/${V}/include/objc/
 lib/gcc/${CONFIG}/${V}/include/objc/NXConstStr.h
 lib/gcc/${CONFIG}/${V}/include/objc/Object.h
-- 
Christian "naddy" Weisgerber                          na...@mips.inka.de

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