upgrading unsupported version of freebsd, third party software step

good day..
recently I decided to upgrade my freebsd-8.2-release "home server" which i mostly use as dlna server for my TV to latest 11.1-release..
i've tried to upgrade directly to 11.1 (in testing virtual environment prior to real movements) with
# freebsd-update upgrade -r 11.1-RELEASE
and got a failure..
then i decided to upgrade step by step and figured out that it works like so:
8.2 -> 9.0 -> 9.2 -> 10.4 -> 11.1
so my question is:
one of the upgrading process step is third party software upgrade
# portmaster -af
is it OK to do it once at the final step 10.4 -> 11.1 or should i do it after every major version upgrade?
 
Go from 8.2 to 9.3 (latest patch level). If I recall correctly there was a bug in freebsd-update(8) that would prevent further upgrades. That should be fixed in the last patch releases for 9.3. Then from 9.3 you can leap to 11.1.

But if it's this old you may want to consider reinstalling from scratch. I'm not sure if the old partitions are large enough for 11.1 and you may run out of disk space on small partitions.

one of the upgrading process step is third party software upgrade
# portmaster -af
I would recommend switching to packages, that will save you a lot of time. Just pkg-static upgrade -f.

is it OK to do it once at the final step 10.4 -> 11.1 or should i do it after every major version upgrade?
You may run into problems if you do it last. In the mean time your OS will have upgraded a couple of major versions but not the rest. So you will see lots of errors and things not working. You could install misc/compat8x, misc/compat9x and misc/compat10x to temporarily fix the inevitable library issues.
 
SirDice, thanks for your answer..
Go from 8.2 to 9.3 (latest patch level). If I recall correctly there was a bug in freebsd-update(8) that would prevent further upgrades. That should be fixed in the last patch releases for 9.3. Then from 9.3 you can leap to 11.1.
unfortunatly 8.2 -> 9.0 -> 9.2 -> 10.4 is the shortest way to 11.1
otherwise it gives "The update metadata is correctly signed, but failed an integrity check" every time you try to upgrade other way.. at least for the day i've tried it was like so (tried it one more time before posting this)..
also i've noticed that there are some problems with package db after major upgrades, i.e. pkg_info (pkg info) not showing some previously installed packages and it is not good..
anyway i wasn't able to resolve an issue with tls support of some cli utils that i use, after upgrading to 11.1, so i've decided not to upgrade.. when time will come i will do a clean install of what version there be X-RELEASE..
thank you again for advise..
 
also i've noticed that there are some problems with package db after major upgrades, i.e. pkg_info (pkg info) not showing some previously installed packages and it is not good..
Oh, right. Completely forgot about that. The package manager changed, FreeBSD 8 still used the "old" pkg_add commands. From 9.x and onward you need to convert to PKGNG by using pkg2ng. From 10.0 and onward only pkg(8) will work, pkg_add and friends have been deprecated and removed.
 
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