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Paths to Immortality in the Hollow Worldby Andrew Theisen
After reading your comments, I thought I'd better take a look back at the paths to Immortality and maybe reassess my earlier comments. Some thoughts after re-examination (note: all comments based on the original Masters Set paths to Immortality, not WotI, which made some changes, notably to the Paragon):
Quest: Finding an artifact that allows time travel shouldn't be any more difficult in the Hollow World than in the Outer World.
Trial: This part could conceivably be a lot more difficult in the Hollow World, since it involves assisting descendants in retaining their kingdoms. I could foresee difficulties with the Spell of Preservation that might not be as problematic in the Outer World.
Testimony: Again, this could be more difficult, depending. One probably couldn't, for instance, create their own nation in lands that are not tied to their origins (ie, Traldar in Milenia), given the Cultural Biases involved. And even taking over or creating a "breakway" nation within one's homelands might be a lot trickier than in the OW.
Task: This ties in with the Testimony, in attempting to create a dynasty in one's new kingdom.
Quest: Finding an artifact from the sphere of Thought is probably just about the same as it would be in the OW.
Trial: Destroying an artifact of Entropy. This shouldn't be any more difficult in the HW than in the OW. There are several Entropic artifacts already known to exist within the HW.
Testimony: Again, these should be no more difficult within the HW than the OW (train a successor; create a legendary weapon). Probably more easily accomplished within lands of one's native Cultural Bias than abroad.
Task: Like the Testimony, this shouldn't be any more difficult in the HW than the OW, but probably more readily accomplished among one's native lands than elsewhere.
Quest: Find lesser artifact of Energy; similar difficulty.
Trial: Creating a new magic item is probably of a difficulty level relative to the sophistication of one's culture; Milenians would probably find this easier than Neathar, for instance. The magic limits of the Spell of Preservation might hinder this somewhat, if only in restrictions of creativity and limiting it to very accomplished spellcasters (ie, Wis or Int 16+, as needed to cast spells in the first place.)
Testimony: Recruiting and training apprentices is going to be a lot more difficult in the Hollow World, due to the ability requirements of spellcasting (see above). Transforming the land may or may not be any more difficult than in the OW; I'm not sure yet, I could argue it either way.
Task: It would actually be easier to be acknowledged the superior of other spellcasters in the HW than the OW, given that spellcasters in the HW are more rare.
Quest Questing for artifact should be of the same relative difficulty, I'd think. The reincarnation wouldn't have much (if any) of an impact in the HW, aside from roleplaying difficulties from Cultural Bias (ie, a questor reincarnated as a magic-user among Antalians).
Trial: No difference here.
Testimony: No difference here.
Task: See Quest, above.
Offhand, it looks like Epic Heroes and Polymaths are the most likely paths for a HW character to undertake, with Pargons being next, and the Dynast being the most difficult.