I’m not quite sure what you’re asking for but this link — which describes all kinds of ways to properly update WordPress — might prove helpful:
http://codex.wordpress.org/Updating_WordPress
And this link talks about managing plugins. Which might be helpful in regards to updating your five old plugins:
http://codex.wordpress.org/Managing_Plugins
Beyond the above, I strongly recommend keeping your site, theme, and plugins as up-to-date as possible. Not just for bug fixes and new features, but also stronger security. See this link for more on this topic:
http://optimwise.com/why-update-wordpress-and-plugins/
Note that you most certainly do not have to start from scratch. Just update what you already have! The only exception would be if an updated (i.e., compatible with WordPress 4.1) theme and/or plugin(s) isn’t available. But even then you could a) reach out to the theme and/or plugin(s) developer(s) and ask when an update is coming, b) find replacements that are WordPress 4.1 compatible, or c) make your own replacements and/or commission someone else to.
P.S., Sometimes a theme and/or plugin(s) say they’re only compatible up to a certain WordPress version yet still work as expected within a later version of WordPress. Thus, if you’ve got an older 3rd party whatever, just test it within your newer WordPress version and see what happens. Any bugs you find can be reported to the developer. Which could end up being just the motivation required to generate a newer version of the currently troubled theme and/or plugin(s). 😉
thx Randy for the quick replies…I will read all the links you suggest.
I have read something from WP re the proper way to update…it said I can really only do 2 versions at a time.
I’m assuming you would suggest I do the above first….then update the Responsive theme….then the plugins?
You’re very welcome! 🙂
I would most certainly follow whatever guidance the WordPress folks advise. Being that they should know WordPress best! 😉 Do be sure, no matter what, to back everything up though.
That being said, to answer your second question, I myself usually update my theme and plugins first then the WordPress core. But, even if I do the reverse I always, always switch back to a default WordPress theme first, deactivate all plugins, then update WordPress on my personal sites. Then I reactivate the theme, then the plugins one at a time. This way, if there is some kind of incompatibility issue, I’ll know the 3rd party culprit right away!
As for commercial sites, or sites with high traffic, I test the update on a development then staging site first. This way, when I update the production site I can be as confident as possible that everything will go as planned. LOL, of course nothing ever seems to go super smoothly, so I always have a backup/restore plan at the ready.