First I would suggest choosing a update source code. TBDev has outdated code and no longer has a support forum dedicated to the source code. If you really like the code there is another source code that is based off of it called U232. U232 source code should have all the mods that TBDev had if not more.
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1. The tracker/site is hosted in two dedicated servers (site/forum + DB) for no reason right now due to low traffic. I think!... I need to save money and move it to a cheaper server. *What* are the specific things I need to keep track of for a smooth migration????
e.g. how can i check if it's "memcached", what daemons are necessary. etc....
Or is it just a "regular" migration as for any other dynamic (PHP + MySQL) site???
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If you are running 2008 source code then AFAIK there was no memcached added to that code. The migration should be about the same altho you will have to change some setting since your forum and MySQL database is currently being hosted on a different server.
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2. Except for everything under /var/www/* and the MySQL dumps is there anything else I should backup for the migration (and for daily backups later on)???
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If you continue to use this source code I would suggest backing up the error logs so you can go thru and make sure all errors have been fixed.
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3. Is there a reason someone with a 2008 version will install mods etc. and still not upgrade to 2009??
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I would say lack of knowledge in coding area, laziness, or just don't care.
I would suggest taking a look at the other source codes out there that still have developers supporting them. If I were you I would keep the site on current servers, then get a new server and install a new source code on it. Then you can begin to convert your mysql database over to the new source code.