A couple of observations that may help folk. If this is not the right forum for this sort of advice please advise:
-- I'm going through the Roosevelt letters and a LOT of them are multiple pages of the letters over several postings -- it is a HUGE help if you look at all the pages of the letters, not just the one or two in the immediate box. This helps with context that can help translate those odd squiggles into real words.
-- Wikipedia is your friend. I just got done reviewing a very good transcription of letter to Teddy from a guy named Eugene K. Austin talking about his ancestor, Stephen F. Austin with from (squiggle starting with a T) and whose father was (squiggle looking like M-something, maybe). MASSIVE kudos to whoever got that far. Wiki tells me that Stephen F. Austin is from texas, was one of the founders of the state, and his dad was Moses, and Eugene is writing to Teddy about his family archives because Teddy writes histories. I got a lot of this from looking at all t he pages of the letter and putting 2 and 2 together.
This may be coals to Newcastle for a lot of folks but it's my daily discovery.