So, now it's November and snow will start falling and there will be even fewer buyers in that area (the prime market to sell is April to August) so I'm facing a dilemma: do I rent the place out and start getting a steady cash flow or do I hold on until spring and hope to sell it for enough to break even or earn a little profit?

You did include lawn care, but, how about snow removal?

Landlords typically pay trash removal, water, landscaping, and snow removal.

Massachusetts like any other state in northern US gets snow, for those who lived in Boston 2014-2015 haven’t forgotten about the 9 feet of snow that we had to shovel or tried to.

@David Luu I'm not interested in living in cold-weather US states where there are hail, snow, ice, tornadoes, hurricanes, 100F daily weather, or subzero winters.

Once you get to this point, make sure to run your numbers for both while living in the house hack (lowering your living expense to less than what it would be to rent in your area) and post move out where you need to be at least break even after accounting for your monthly payment + maintenance, capex, vacancy, property management.Here's a great resource right here on BP:https://www.biggerpockets.com/real-estate-investing/house-hacking-strategyMost of the podcasters started out with a form of house hacking to get their snow ball rolling. 

Quote from @Adam Snow: Hey @Eric Lish I am a local real estate agent and investor in the Birmingham area.

Afternoon all, anyone have a good vendor that does snow shovel/salting in the Garfield Ridge/Clearing neighborhood in Chicago just west of Midway? 

So while the numbers of having 5 offices look better INITIALLY, when you count in utilities, lawn care, snow removal, repairs, property taxes etc I wouldn't be so sure, UNLESS you can rent-out each office for more than $1,000/mo?

We don't get the snow, so we rent up any time of year.