Linking from old to new website, with similar content

link from old website to new website

[zorogat]

Hello,
i have a website with an average 1500/2000 visits a day , mostly from Google, and a decent income from Adsense.
This website ranks in top 3 google serps for many keywords and all the content is free to read.
Now i'm developing a new online application, but i don't want the application to be free: users must pay a small subscription fee to use it.
This new application targets exactly the same keywords of my old website and the content of the app is very similar to the one in my website, but much more detailed and focused, hence the fee.
Of course what i'd like to do now is to use the stream of visitors from the search engines that come to my old site and redirect them to my new application.

I came up with two different solutions for this:
1) add the application to my old authoritative domain. in other words, create a new section of the website that is not freely accessible
2) start with a brand new domain in a different server and link from the homepage of my old authoritative website to the new app.

I personally would like to keep the new app separated from the old website, and i'd go with solution number 2, BUT i'm worried this could cause some trouble in the serp for the old authoritative domain.
The old website has very few outbound links (none in the homepage) and a new link to a brand new website could damage it.. or not?
What is your opinion and experience with such a dilemma?
Thanks you in advance to anyone that can help me with this one..
Zorogat

[bleached]

I recently had the same dilemma which is addressed here: [webmasterworld.com...]

A month has gone by since this post and the only advice I can give by my experience is that if you want to link any sites together use the nofollow, or better still, not at all. My authoritative site dropped heavily in traffic after linking to the new website, however gave an initial surge of traffic to this new site. Keep them separate entities I think is the best bet, it also won´t risk your authority site.

[zorogat]

thank you Bleached, that thread is really interesting, and you are really helping.
so you actually had a drop in traffic after linking to your new website... that's quite scary, isn't it?

what about having the new not-free section included in the old domain? what i mean is, my old authoritative website would go on publishing its free articles, but i'll add a not-free section, with different content and different interface in the same domain, linked from the homepage..
do you think google would penalize me for that?