can I repurpose a Page?

I have an 11 year old smaller kindof directory site with under 10 niches - several being local offline businesses. Over the last year I have realized my online seo capabilities and have been moving full force into various difficult niches with good success. Do to health reasons I am leaving New York...and am having headaches trying to rent the local prime real estate that dominates the front page of my site for such little local trafic. I am highly considering to stop wasting my time and cut my losses as there are so many more profitable things I can do with the front page of the 1000 page site than to bogg it down for $35,000 a year and a headache of even getting paid. Long story short, if I shut down 15 pr4 and 1 pr5 page for local services, that happen to have the local areas and service keyword in the url,(yes rather long url's), can I repurpose these pages for something completely different? In other words how much relevance does the keyword rich url have anymore with new algo updates. If I turn what is currently an established home remodeling page into a dating site promo page will I have salvaged some of my investment that it took to build this page up, or will "G" just think im crazy. BTW there are no worthwhile offers related to remodeling considering its low quantity local traffic, and going for more global traffic doesnt look like it will even be very profitable either. I would consider shutting the page / pages and doing 301 redirects to new pages with different subject matter, but I recently had a bad experience last August I moved a static article directory to wordpress backend CMS....did hundreds of redirects.(ex: 54 pr3 category pages were redirected to the new WP categories of exact same subject matter....and none of the pr ever transferred....and I dont even think the previous links are counted.....it was done right as well.) so do I entrust in 301's and toss the pages? (i realize the second issue is that all backlink anchors are remodeling related, but they should still be better than starting from scratch), or do I just change the content of the page....start to build appropriate backlinks for the new completely different niche and deal with the unrelated url.....im not really concerned of the url looking awkward to visitors as the page is going to kind of be used as a presell for a product such as IM, weight loss, dating etc. visitors wont even realize the url of the page, only perhaps the page they get funneled to. Everyones help is greatly appreciated on this one. Remember, remodeling is just not a desperate enough niche for me, and new places pages just hog up results globally, so im not interested in looking for a related offer. This is about saving my invested money and energy it took to create this department and repurposing it. And I know I could just try it, but if I move forward, I will do heavy backlinking and marketing for the new page to prepare it to compete on results pages with over 100,000,000 competition......yes the zeros are correct--I have already done this with one of my niche pages in <90 days recently and it was a brand new page and aggressively seo'd. What would you do my senior and experienced warriors?

Thank you to All my Fellow warriors as my head is about to explode on this one.

Dennis