Nick,
Sounds like you have a good strategy. I only have two additional items to share based on your latest reply.
www.url.com/resort_hotels/hotels_in_rome.asp
That url seems a bit spammy to me. Mentioning "hotels" twice is something I would avoid. I would consider something along the lines of the below options instead:
www.url.com/resorts/hotels_in_rome
www.url.com/resort_hotels/rome
www.url.com/hotels/rome
I also wanted to talk about the landing pages for cars and air travel once more. Before directing all your current pages to a generic page I would take a look at the existing 140 pages and ask once again, do any of the pages have anything that is unique which can be used for the location based car and air landing pages?
Your plans are to develop these pages with quality content over time, which is great. I hate the idea of having establishing pages for each area, pulling back to having one generic page, then expanding again to location-based pages.
If you sincerely intend to develop these pages on a reasonable time period, I would suggest establishing one page for each location even if it was thin on content to start with. Driving directions, local driving laws, testimonials, anything that can be used as a starting point to hold your footing would be preferred.
If you do pull back to a generic "car rentals" page, I have two ideas. Build out your location landing page for one area such as London. Closely watch your conversion rates on users on the London page versus the generic page. If there is a significant difference, it may help speed up your transition. If you realize you are losing $$ every day you don't have those pages, then perhaps you can hire additional help to speed up the process.
The final idea would be to build country-based landing pages for car rentals as an stop-gap measure. Your Milan, Rome, etc pages could all direct to "Cars Italy" and "Air Italy".
There are tons of choices on the internet for travel providers. You have an extremely well established user base. My top concern for any migration is to maintain all my existing relationships. Some travel sites do great with a single landing page for air/cars/hotels. It sounds like your site has catered to clients in a specific way, and I would be sensitive to maintaining your current user experience.
One last idea that just came to me. After the migration poll users for feedback. Take surveys, offer discounts, generate hype but engage users because they will offer a different point of view which you may not have considered.