The economics of "You Know Me Al"

Ring Lardner's You Know Me Al traces the (self-told) adventures of a promising young pitcher who has just signed on with the Chicago White Sox.  It's a little unclear when the stories are set, but we know Lardner arrived in Chicago in 1907 and the first You Know Me Al story appeared in The Saturday Evening Post in 1914, so that's the approximate era.  Kid Gleason is assistant manager but doesn't appear to playing, so that means it must 1912 or later.

Perfect:  the BLS inflation calculator goes back to 1913.  So let's see what our hero was spending on his way to the Big Leagues.  (These are taken from the comic book version, scripted by Lardner, and collected and reprinted in 1979):

• While still in the minors, Jack asks a player on another team what it will cost to live in Chicago.  "How long are you goin' to stay?"  "I'm goin' to be with the White Sox."  "Oh, about twenty one dollars ought to see you through." --> about $500, good for a month or two at the most.
• Jack orders a small sirloin steak in a fancy restaurant, $1.75 --> $40 in today's money.
• Later we see him walking, with a big smile, into a restaurant advertising t-bone steak for $0.25.  That's $5.90, much better
• Jack meets Chicago owner Charles Comiskey, and demands $5,000 ($118,000) per year.  Comiskey tells him to come back when he's sober.
• After carefully explaining that the taxes on $5,000 will ruin him, Comiskey offers to pay him $5,000 for two years instead of one, to spread the tax bill out over a longer period.  Jack accepts this generous offer, so signs for a still-nice $59,000 per year.  Median family income in that era would be about 1/4 of that.
• Jack rents a room for $8 week (after seeing the landlady's cute daughter).  This is no bargain, unless you count the daughter - he is signing up for about $755 month, although it does have its own bath.
• Later the landlady offers to make him breakfast and dinner every day for an extra $10 per week ($40/month), or $940 per month in today's dollars.  $30/day for breakfast and dinner is a bit rich - the landlady seems to have figured out math isn't his strong suit.  

From the book:

• Jack sends a girl $30 for the train fare from Cleveland to Chicago, about $700.  She wanted $100 so she could buy clothes, too, but he tells her to buy the clothes when she arrives.  She calls him a cheapskate and keeps the money.  (Not clear if it was supposed to be a round-trip ticket.)
• "Then [in Boston] I went down the Main Street again and some man stopped me and asked me did I want to go to the show. He said he had a ticket. I asked him what show and he said the Follies. I never heard of it but I told him I would go if he had a ticket to spare. He says I will spare you this one for three dollars [2013: $70]. I says You must take me for some boob. He says No I wouldn't insult no boob. So I walks on but if he had of insulted me I would of busted him."
• "I have gave up the idea of going to Australia because I would have to buy a evening full-dress suit and they tell me they cost pretty near fifty dollars [2013: $1,200]."
• After baby comes, two minor doctor visits (house calls), $2 each [2013: $47].