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Generally, as a solo warrior it is particularly important to equip yourself properly first, and then to a lesser extent worry about which Level you’re at. Put together a ‘shopping list’ of items to go after or purchase.
I would suggest that you deal with your capacity to protect yourself from Level Drain as a high-ish priority. The other factors are to protect yourself from the numerous mind-based attacks. The capacity to summon, such as found in the Elemental staves, will probably prove to be another obstacle-breaker. The capacity to disappear from a fight that might happen to be going against you will probably be another matter to consider.
The first two levels of Watcher’s Keep are fairly ‘do-able’ at an early stage of the game if your solo warrior is well equipped. For me, at least, Level 3 of Watcher’s Keep is generally left until Chapter 6 where (normally) your Higher Level Abilities are kicking in. There are some traps on the first two Levels of the Keep, so the capacity to cast Mirror Image will be handy.
As for "the best time" I guess it's personal, although for me; I don't consider going into the Keep until Chapter 6. Unless you particularly want an item of equipment that resides on one of the top two levels, I wouldn't suggest that there's any great need to charge in earlier than Chapter 6.
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