This is the route I would go when moving over to WP.org.As far as switching server and hosts, that doesn't much matter in this case as long as all the content on your site stays the same (or are set up as a 301 redirect https://moz.com/learn/seo/redirection).  

@Neal Patel (your name is very similar to the SEO guy I follow...

Just a one off, I use to have a marketing team and SEO/PPC at my fingertips, but for this property I don't

Which sites are winning the seo war when you search in google?

Maybe, I’ll be in a place to learn SEO sometime soon.

For example, maybe you send a certain amount of direct mail, or spend a specific number of hours on SEO, or drive a certain number of neighborhoods.

Do this now and if you apply the right strategies, you will have a #1 ranking website just in time for spring.Get a website, and absolutely go for Carrot.Then focus on SEO and your credibility.Don't just wing this.

SEO generates, free high quality traffic to your website.

To answer your question, I do not have much organic traffic but also have not spent much time on SEO yet with my dedicated site and mostly leveraging paid traffic.  

Individual ones tailored to your target audience (motivated sellers, buyers, wholesalers) with:-1) Testimonials (built over time since I'm a newbie)-2) Blog posts-3) Linked YouTube videos-4) Simple info take-in formB) Free Craigslist adds regularly-updated that direct to that professional website(s) C) Paid-per-click advertising to get people in the door (Google/Facebook ads, etc.)D) Combine w/ OFFLINE marketing strategies (i.e. signs, car magnets, mailers, radio spots) directing folks to your domain name that you made easy-to-remember E) Best website would also have a cross-over to CRM with direct alerts (texts to my phone)For long-term optimization of foot traffic and conversion:A) Manage that SEO (continuously or pay for someone to do it)Am I missing something?