I’ve been playing a hobo run on 0.8. He broke his alcohol addiction on day 4, and that’s with the “addictive personality” penalty (seemed fitting from a role playing perspective). I had ~8 or so drinks on the first day to give me enough time to collect some decent clothing and pack myself out with food (cans of beer are actually great early-game food for an alcoholic). 1:30pm on the first day was my last drink. I wore whatever mouth protection I could find after reading this thread. Ended up catching a cold but never the flu. I also managed to find some vitamins in the first couple of days and took a couple every time I woke up. I looked in the code, and to drop your addiction level at first, you need to stay sober for somewhere around 10-12 hours. If you take a drink before that, you negate any progress. I went cold turkey, so it didn’t really matter.
Since you don’t have alcohol cravings while sleeping, I would always try to either craft, read, or practice fighting as soon as I woke up while my focus was high. Since I slept so much, my HP kept refilling, so I could afford to take a little damage while fighting. Withdrawal affected my stats, but not my speed, so I could still melee pretty well. Once the alcohol cravings bombed out my focus, I would go back and try to sleep more.
Anyway, filter mask + vitamins does indeed prevent illnesses pretty well while recovering from addiction. The cold had very little affect since I wanted to take Nyquil anyway to sleep. I know the theme of this thread is that hobo should be made easier, but with the right strategy in place it seems too easy already. My last run took 8 days to go sober, and this one only took 4, and after that, I have the rest of the game to enjoy my 4 free stat points.
By the way, I used those 4 points to boost strength by +1 and then get the krav maga fighting style. I guess that means my character is an Israeli who moved to New England after he served his 2 years in the military and then lost everything… not sure how else a hobo would know krav maga.