Is it a waste of time to put the 14 cities' websites on domains that we own (i.e. domainnyc.com, domainsf.com, etc) and then move them to the subdomains once the sale of the domain is completed (which could be more than a year's time)? WIll this result in lengthy delays in the search engines?
If it's being held by a speculator, what leads you to believe you'll actually get the domain in a year? If the deal's going to happen, it should probably happen now. Delay would probably drive up the price, especially if/when the speculator gets wind of what you're planning to do. Or what if someone else see the connection in your other domains and figures out what you plan to do, forcing a bidding war on the domain?
[P.S.]
Also, what happens if the speculator decides to play with the site before selling it (e.g., lets a SPAMMER use it and it gets blacklisted, gets it blacklisted for Google AdSense, etc.) Do you have backup domains in mind in case something like this happens or if the speculator sells to someone else?
Let's assume that finances aren't an issue
Then, if that's the case, buy the domain and build the websites as subdirectories.
If your concern is for search engine love - whether your actions (redirects, etc.) will assure a safe and smooth transition - AND IF such love is integral to your company's business plan I'd say scrap any plan other than building on the desired domain using a clean-optimization approach. Clean = designed for usability and user experience, CSS built, logical titles and file names, lay off studies of keyword densites, be wary of aggresive SEO, etc.
There is no contract between you and the search engines concerning how they handle any process. They MAY handle redirects today in a certain way but alter that approach, based upon factors as varied as whether SE spammers are employing a system of sub-domain redirects as an attempt to circumvent penalities or filters.
Yes, redirects are generally accepted as a proper way to keep the SE "informed" and SEs reportedly are friendly to benign redirects. Yes, there is a body of consensus that SEs are capable of shifting PR or other weighting factors based upon a properly excecuted redirect. No guarantees. YMMV.
Search WebmasterWorld for comments by GoogleGuy concerning redirects. I (somewhat) recall him speaking to the issue.
Buy the domain and start getting inbound link love.
One of the tenants of your post is to get the site up there "cleanly" and begin to bring inbound links. The site is created according to your cleanliness guidelines, but I do have one remaining question:
Assumiing that the goal is to bring quality inbound links as soon as possible, that redirects currently do not negatively affect a site's rankings, and that the aquisition of the domain may take many months, why wouldn't it be in our best interest to place each city's site on the web now and simply redirect when the domain is aquired?
Thanks again for your time.
I'd like to think it all will go smoothly, given your proposed process, but there's no guarantees on any of this.
My motto: Don't build a long term business model based upon search engine love. Work on all other methods of building traffic.