I’ve been using WordPress for quite a while now and upgrading seems second nature TBH. I’m quite lucky all my upgrades have gone swimming well. WordPress is a nice CMS to setup, upgrade and keep tip top but agreed your first time can be a bit “now what”.
Just recently I’ve been getting an upgrade error in WordPress on one of my budget Blue Host servers used for mini sites when attempting to auto upgrade with WordPress’s built-in upgrade option. To version 2.8.5
Fatal error: Allowed memory size of 33554432 bytes exhausted (tried to allocate 2354671 bytes) in /home6/main-domain/public_html/domain-name-co/wp-includes/http.php on line 1331
Basically I think the server is throttled and WordPress kicks off because of it.
Few ways to get round it.
Hope one of them works for you but a few other plugins I’d suggest to install to safe guard your WordPress install are
Keep backed up, updated, be careful of rouge theme’s with dodgy coding and all should be fine!