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I'm glad you joined. Hunsterverse is pretty great for the PSP games. I haven't picked Dos up for about a week now. A lot of grinding to get your gear upgraded. I went into the HR patch and was being murdered by everything, it was frustrating. I'll go back when I feel like grinding out a upgraded hermitaur set. Did you guys end up in end game in Dos?
I did. The transition from offline to High Rank is the toughest part, because of difference in gear power that makes even minions a serious problem.
I advise you against upgrading Hermitaur armor. It has bad stats and requires precious materials that could be used to craft better stuff. Imo, a good HR start is upgrading blademaster Monoblos S to lv4. It has very high defense and is relatively easy to upgrade (requires 1 Wyvern Stone for each part, the rest is easy to get).
As for weapons, imo, a good start is getting ancient DS, Hm and GS, as they are strong and don't need you to kill anything in HR. Eternal Schism alone will allow you to kill most of the HR ancient dragons.
The "hardest monster" in the game is HR Black Diablos, because the only quest he is present requires you to also hunt a normal HR Diablos and the HP nerf when there are multiple monsters is insignificant compared to MHFU and MHP3.