can yearroundrentals.com become rentmyplace.com w WP?

I’m exploring the conversion of my high ranking real estate platform (since 2003) from PHP to WordPress + optimized for iPad2 (+ or App).

The site would look like national vacation renal site but be for long term rentals instead of weekly. I love it but have not seen many significant real estate organizations using it. Eager to make a move and not sure if WP is the right architecture. This is not an MLS driven website.

I welcome advice and blunt guidance. Thank you!!

Curent site:
simple php real estate vacancy posting site
owners and brokers have simple account functions; post, my listings, change password, add listing, add company banner etc.

Minimum New site specs:
Don’t lose #1 rank.
Wordpress Platform
Your recommended CMS for b-plan
Owner and broker account creation, management functions, simple micro sites.
tight high quality display of rental property data; contact, text, pics, video, map.
predominant map based search and display of properties.
ability to input all new property listing data and upload from iPad2.
Google analytics for site and rentals.
Paid Featured listings based on map location
Simple Micro sites for brokers and managers.
Social media integration, API, Affiliate Advertising etc.
Syndication to craigslist; code to be produced into branded form.
Syndication to others possible.