As an alternate solution, if the site is not too heavy with the features, the entire site can be re-build in Drupal 7. I know its not the "drupal" way of doing things but in the past I've found the method to be fruitful. The 4 important concerns would be:
  1. do you understand the information architecture of the site, d5 and d7? this will be used in content migration
  2. is there a drupal 7 module for all existing modules? if not, do you know how to do it?
  3. is there any custom module? are there documents pertaining to the custom modules? is the code for custom module documented?
  4. is there a base theme? is the current theme a sub-theme? if  not, is there an upgrade path for the theme? if not, do you know how to convert the theme to adhere to d7?
Again, the solution works if you have build the site in d5 and is likely to fail in case you have not.

On Sat, Jan 15, 2011 at 8:26 AM, Dave Metzler <metzler.dl@gmail.com> wrote:
I think Gordon has the answer... Database updates cannot be guaranteed without following the 5 to 6 to 7 methodology.  You will be left with a buggy site as a result.  I agree that there is nothing to say you couldn't never show the drupal 6 site as a live site.  You're just using it to get the schema updates.

Of course if you are doing the work as a consultant, the number one reason that will convince them is that it will cost you more time and them more Money :).  

Of course that's only after you've verified that you have the contrib module coverage that you need...

I hope that's helpful and not all too obvious.

Sent from my iPad

On Jan 14, 2011, at 2:57 PM, nan wich <nan_wich@bellsouth.net> wrote:

That's a good article. I suspect his approach worked because he was already intimately familiar with the site. My task would be to go into a customer's site that I haven't even seen yet, let alone explored internally.
 
However, the question is what to say to the customer, not how to do it.
 

Nancy

Injustice anywhere is a threat to justice everywhere. -- Dr. Martin L. King, Jr.



From: Randy Fay <randy@randyfay.com>
To: development@drupal.org
Sent: Fri, January 14, 2011 4:45:55 PM
Subject: Re: [development] Upgrading Drupal

You have to upgrade from the last Drupal 5 to the last Drupal 6 and then to Drupal 7.

Quicksketch posted an alternate approach: http://quicksketch.org/node/5739

-Randy

On Fri, Jan 14, 2011 at 4:39 PM, nan wich <nan_wich@bellsouth.net> wrote:
I suspect I know the answer but am looking for reasons to convince a potential customer. The question is: Can you jump from Drupal 5 to Drupal 7 in one fell swoop? I see upgrading contribs as one of the biggest obstacles with API changes being the next one in line (assuming there is site-specific custom code).
 

Nancy

Injustice anywhere is a threat to justice everywhere. -- Dr. Martin L. King, Jr.




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Randy Fay
Drupal Module and Site Development
randy@randyfay.com
+1  970.462.7450




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Cheers,
Mukesh Agarwal