Agree with the above and would like to build on it a bit - my background is similar to yours (math undergrad, got the equivalent of a MS-stats via industry training programs, active Python hacker who developes in other languages).

First - don't underestimate the value of your math skills vs. your programming skills; I busted six figures as a stats geek long before my technical skills got into that range. If you're good at math, this is rare & valuable - particularly if you're also good at talking to people. (Those people are called analytics directors and it's a nice way to make a living; plenty of paid hacking time).

Second - agree you should consider leaving MI - NY or Boston sounds particularly a good fit; I'd look at the financial industry. While the work can be soul-sucking, you can build a nice bankroll relatively quickly in that space that can fund other interests.

Third - You should definitely expand your search beyond Python. While Python is my language of choice, I also attend PHP meetups and (infrequently) events targeted at Oracle and Microsoft developers. Here's some (bigoted) commentary comparing the different groups:

- I've found the Python groups to have smarter hackers relative to the other groups; the talks tend to go much deeper into the underlying technology/computer science behind the topic and the dinner conversation is better.

- Many folks at the Python meetups are employed in roles where their focus is using other technologies (lots of Java, some C++, several DBA/sysadmins - Oracle, SAP).

- Recruiter activity is fairly low at the Python meetings (0 - 2 recruiters per event); most recruiters who come are hiring for non-Python roles. I find this amusing, since I've identified this group as the best source for my next analyst hire and/or technical cofounder connection.

- The PHP group across town is about 30% larger and tends to be a bit "fluffier" in terms of presentation content. The technical skills of the average developer at these events is a full order of magnitude below the Python folks - when discussing equivalent issues, the average PHP developer has a looser grasp of system internals, how the algorithms inside the box work, and subjects such as OOP and functional programming.

- We have a TON of recruiters and hiring managers working the PHP meetup with relevant web development jobs. There are generally between 3 - 5 "announcements" per session; generally from folks with LONG lists of jobs that use PHP. A surprisingly large number of these want simple framework developers, which I see as significantly less rigorous than the stuff my Python buddies are working on.

- And to fully explore the dark side of the force - I've run into tons of recruiters looking for Java, MSFT, and Oracle people; also seen demand at good pay for closed source packages (SAS, Microstrategy, Saleforce.com). I'm talking about drag and drop stuff that developers would laught at. I've seen SAS analytics rates which rival a director's pay - and aren't very rigorous from a technical perspective (started my career as a SAS programmer working on statistical analysis). Did you do SAS in college?

So - many options, definitely look outside Python and leverage those math skills.

True Confession: Despite having some nicely developed programming chops in Python/PHP/Javascript, my bills are being paid by my analytics day job - where my relatively high priced existance is being rationalized by (wait for it)... analytical applications I built using Access VBA, Oracle, and Sharepoint. Stuff that makes real developers laugh hysterically. Seriously - we're making millions of dollars a year off of these applications, most of which were cranked out in under 2 - 4 weeks of core dev time. The latest round of miracles does use Python, but the "cash cows" which have protected us from layoffs... straight up SQL and Object Oriented VBA... go figure.

Point is - focus on the application space, use your highly valuable quant skills, and, if you need the cash, don't be afraid to use corporate technologies and lower end stuff.