I'm trying to shrink the file size of a massive log file and was wondering how I estimate the size of the log file and what the dangers in running this are
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If you use the full or bulk logged recovery model, I advise that you take a look at this post for shrinking the log file. First perform a full database backup as switching the recovery models will break the log chain. Also chose a reasonable initial size for the log file, and generally speaking I use an increment in MB rather than percents.
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What is your database's recovery model? If FULL you can Shrink(Back up with no log). if recovery model is simple, SQL manage the transaction log file.
You can shrink log file successfully once the transaction log was commit(Full recovery model). As far as i know, i have concern once your transaction log file get auto grow again, it might takes time to reserve space. You might get problem IO overhead.