So here is my two cents on PVP based on High Sec War Decs, Low Sec Roams, Some Null and Some WH experience. I do not profess or hold myself out to be a good PVP'r. I can not rattle off ship names and classes, ecm races and types, and many other things. But I do think I have a feel for what PVP entails.
In addition I think I have the three main keys to starting into PVP.
1) A willingness to learn from others
2) A willingness to try
3) A willingness to die
With these three things as a basis I think anyone can learn and enjoy PVP.
To be clear, this is also almost entirely from a perspective of small to mid sized fleets (3-15 ships).
To start it might be easier to define what PVP is not. PVP is not an extension of PVE. It is not a progression from L1 to L4 to C5 anomalies. And most of all it is not Fair. The fact that they brought 8 guys when you brought 3 is not unfair, its smart.
I have seen many people who think they will rock at PVP because their Raven setup "kicks ass" on Level 4's. They are naive and ripe for failure. A fleet of 3-4 small ships properly fit and flown by good PVP'rs can easily take out that shiny Raven, leaving you wondering how you just lost your 300M isk setup that crushes L4's. I have seen Tengu's go down to fleets of ships worth less then 100M total.
PVP is a completely separate aspect of the game and as such requires different skills, both in game and real life, to be successful.
In my opinion there seems to be several "Steps" in learning and being comfortable at PVP, each with a different skill set and scope of knowledge.
Step 1 - T1 Frig - ISK involved $500k-$1M
Pick your race's best frig. Only requirement is at least 3 mids. Requires AB, Warp Scram, Web. Fit highs for best DPS, lows for cap stability and added DPS. NO EWAR. Learn to do 4 things in order. Orbit close and fast (ie get differential speed maxed), warp scram, web, fire. Congrats you are PVP'n now. Principle here is simplicity. You have a role in a fleet (tackler) and you are adding to the fleet's effectiveness. You will get over the jitters of PVP and risk very little. Just remember to always update your Clone after you die.
Step 2 - Cruiser Specialist - Isk Involved $10-20M
Now learn your race's cruisers. There are some awesome EWAR and Support cruisers as well as some decent DPS boats. Key here is to start to find some niche to fill. Blackbird/EWAR, Aurogor/Support etc. You now have to start to expand your skills and worry about others around you. You will have to start to understand primaries and secondaries, optimal ranges. You will have to learn to walk and chew gum. You will die, especially in a Blackbird. Just remember to always update your Clone after you die.
Step 3 - Battlecruiser - Isk Involved $40-50M
Now its time for some bigger toys. Legit DPS. FC'n and making tactical decisions (as a step the FC might be in a Frig for a Frig Swarm, but should probably be at this level of comfort to be able to make decisions about others.) Overall the skills here are understanding opponents, making decisions about primaries, understanding what the opposite side is using and how to counter. Also should really be able to deliver some serious DPS. At this point you might also start to be able to dabble in solo PVP.
Step 4 - BS, Tech 2, Tech 3 etc. Isk Involved - $50M to whatever you can afford to lose.
Here is where the specialization really starts. Falcons, Rooks, Curse, SB's, Zealots, Guardians. Here a role is well defined and you better know what you are doing. You have a task in the fleet, a job to do and people are depending on you with their ships to do it. DPS, EWAR, Support, HIC, Bubbler. The roles must be balanced by a competent FC as it is very easy to have 1B isk plus in play. Here is where enemy knowledge and fleet setup have as much if not more to do with the success of an encounter then individual skills.
I feel I am at the very early stages of Step 3. But no matter where you feel you are, with an open attitude, willingness to try, and willingness to die you can progress.
It is also more fun then watching the paint dry inside the station while a single Red Zealot come looking for you and your corp mates.
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