Chikki Chan KingdomVolc Python and C# have very little to Trickster Online binaries since they were made with C++. Programming in general has very little to do with setting up a Trickster Online server since we only have binaries, config files, and a database to work with.
If you do plan on running a Trickster Online server, then I do suggest you learn SQL, specifically T-SQL which is what MS SQL Server uses though MySQL knowledge will suffice if you have a T-SQL reference sheet nearby with the different nomenclature highlighted.
As a matter of policy, I would deter you from using anything microsoft-related unless you must use it. In the case of .net and asp, for example. Speaking of which you will probably need some knowledge of ASP or PHP for an actual public server for the cash shop.
Now as for learning to program in the first place, we have a section for that:
Coder's Paradise
Though I would hardly recommend it as a good source, conversation about programming belongs there.
My suggestion is to pick up some "How to learn *blank language* in 24 days (or hours, it varies)" books.
As for suggested path to learn C++ is:
Python > C > C++
If you have the aptitude for programming that should work for you.
Programming isn't something anyone can be good at without talent for it.
Programming is an art, those with talent for it will always have the upper hand.
Doesn't mean you won't have to work hard even if you have talent, so keep trying.
Mistakes are good chances to learn, so make many of them while learning (on purpose if possible) as they lead to a better understanding of the material you are covering.
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is a link to some downloadable books you can learn Python from.
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is a link to a (simplified) tutorial for SQL and the differences between the various types.
Unless you are going to do some reverse-engineering, setting up a Trickster Online server does not require any programming languages.
(SQL stands for Structured Query Language,
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is a scripting language, and ASP stand for Active Server Pages and is also a scripting language like PHP)