Redirecting from Wordpress.com site to Wordpress.org with SSL

Question

I am in the process of transferring a Wordpress.com site to Wordpress.org.

The old site domain: https://oldsite.wordpress.com.
The new site domain: https://newsite.com.

I am facing a dilemma on the issue of redirects.

Wordpress.com's redirection service support page states:

Note: Site redirects will only point to a non-ssl ( http:// ) url.

So as far as I can tell, wp.com will redirect https://oldsite.wordpress.com/2014/10/21/sample-post to http://newsite.com/2014/10/21/sample-post (notice, not https).

The new site (stored on GoDaddy), will then issue an HSTS redirect to the https version.

As the new site uses a different link structure than the old site, another redirect will then be required using a Wordpress.org redirection plugin.

So altogether, from what I understand we will have this series of redirects:

https://oldsite.wordpress.com/2014/10/21/sample-post/

    |
    | Wordpress.com redirection service (301)
    V

http://newsite.com/2014/10/21/sample-post/ (does not exist)

    |
    | HSTS redirect via .htaccess (301/307)
    V

https://newsite.com/2014/10/21/sample-post/ (still does not exist)

    |
    | Wordpress.org custom redirection via plugin (301)
    V

https://newsite.com/sample-post/ (exists)

Questions

1. Is this really the series of redirects that will occur?
2. Is this the optimal way of conducting this transfer? According to this question, multiple 301's will have a negative effect on link equity.
3. I've seen this question which suggests importing the content while the link structure is the same and then changing it. Does this have any advantage or disadvantage (in terms of link equity preservation) compared to defining the redirects myself via a redirection plugin on the new site?

Answer 1

From what i understand Googlebot will follow around 5 legitimate redirects, so as long as you are pointing users from the old content to the new content you will have no problems. https will actually give you a ranking boost in the long term as with the redirects it looks like you are doing nothing that violates the Google Webmaster guidelines.