I have been trying to upgrade a 3.1 site for a while now.  Needless to say I am in way over my head and have not made very much progress at all. So what I would like to know is if this is even worth continuing or would the best strategy be to build a site from scratch that exactly replicates what I am using now and somehow copy the database over? 

I'm not sure this is the right place to post this question and I apologize if it isn't, but if anyone here has any experience with a upgrade such as this I welcome any ideas with the utmost gratitude. 

I will try to answer any questions that you may have, but I am very inexperienced with DNN.

Stephen - an upgrade is possible.  My own site started in the 3.x days and has been upgraded over time to the current version.   

What will be key is:

- doing the upgrade in major version steps (ie, 4.x, 5.x, 6.x, 7.x).  Others may say this isn't necessary but I think it's a safe but slow way of going.  If you upgrade to each major version then you can check the site each step of the way and verify any fixes.

- if you have third-party code you need to determine the status of the parts for compatibility and have any new versions ready.

- make sure you take backups of files& database after each step, clearly label them and work out as you go.

You should do all of this as a 'dry run' on your local machine or test server if possible, then replicate the steps on your live site.

Good luck and stick with it, the result will be worth the pain.

I tried following the suggested upgrade path here on the wiki, my issues start when I upgrade from 3.2.2 to 4.3.7. I even tried upgrading incrementally from 3.1 onward, at 3.3.0 is when my site stops working completely.  I am not a programmer and have very limited experience with it.  I know that we aren't using any third party modules, but that there have been changes made to the core code when the site was managed by a outside company.  

Thanks everyone for the response, I will continue to work on it and keep posting questions as they come to me.