Regarding the first item, the URLs, it sounds like you intend to update your site in the future which is great.
The second item, using the page's phrase within the content, is an important SEO consideration which I would strongly recommend being used 100% of the time. With that said, you are right in that the pages which outrank you, including the #1 ranked site, often do not use this best practice. I can't comment on that much further then to say SEO is purely a competition. My strategy has always been to take every action within my control to improve results. You can choose to skip various steps as you deem fit. Keep in mind there are numerous significant metrics which Google uses to rank pages to which we do not have visibility. This challenge only emphasizes the importance of maximizing all the metrics within our control.
The third item is duplicate content. I had examined 3 pages on your site and all were the property pages. I simply chose the first 2 properties, and then a third property which had the same title as one of the selected property but was actually a different listing.
My concern is that in your latest example of a "fuller" content page (/Holly Bush Countryside Cottage) there are 126 words in the description. Even if I include the sidebar content the total unique words on the page is 158 out of 1203 words. 87% of the page is duplicate content. It's simply far too much.
With the above noted, it sounds like you wish to focus on your search pages, not your property pages. You mentioned that you added the noindex tag to your property pages. I am not seeing the tag implemented. I have checked the Holly Bush page mentioned above, and the David Carr page mentioned previously. Both pages are marked as index, follow.
The bottom line, your site is very likely experiencing a site wide penalty. The root issue is a very high percentage of your indexed pages are duplicate content. My suggestion is to get control of the situation and begin adding pages back to the index.
Step 1 - create a sitemap for your site listing every URL.
Step 2 - review the sitemap and decide which pages you wish to be indexed. Any page which is not ready to be indexed for whatever reason should have the noindex tag applied.
Step 3 - review the remaining pages. Ensure they are unique pages by minimizing any duplicate content.
If the above plan is implemented properly, Google will notice the changes as they crawl your site. Do not use robots.txt to block your pages as this will prevent Google from viewing the page changes such as adding the noindex tag.
I expect it to take a solid month for Google to crawl all the pages on your site. Once the entire site is crawled, Google will then recognize your site complies with their guidelines. At that point it is likely your penalty will be immediately lifted. It is possible you will be kept in a "timeout" period where the penalty remains for a bit longer, but I would expect the issue to be resolved within 30 days.