I work in Potomac, MD, and would like to buy a condo or apt that I can easily commute and live in, and then eventually rent out, and then buy another. 

Love that you are spending your commute at a mobile university.

Are there alternative strategies you’d recommend for this market or nearby markets which are of commuting distance to Danbury?

Quote from @Ven Bud: After hearing to lot of bp episodes on negative cash flow, I have a question.I am currently living in my primary residence and planning to purchase an investment property, and obviously it is going to be a negative cashflow (bay area), but I am of the opinion that as long as the rent on the investment property is atleast going to be greater than my current primary residence mortgage it can still considered as positive cash flow investment.The investment property is going to be in a much better location (for office commute, bay area proximity) than my primary residence.

I have reserves, but would prefer not to put all of that in right away and hold some money for unexpected expenses.For context, my current monthly housing expenses are ~1250$ including rent, utilities, internet etc in a decent area with a short daily commute.

@Christina ChatzoglouHouse hacking in Union City, NJ can be a smart move due to its strong rental demand, multifamily inventory, and commuter-friendly location.

By no means cheap but solid rent + demand, fun place to live, decent inventory (relatively speaking), and is still commutable to the city. 

Tenants in small multifamilies are often longer time locals of an area and are choosing to live in a specific section of a city, for the schools or for a shorter commute or something.

Berea is extremely difficult for renters to find low price points and they’ve pushed themselves deeper into Eastern KY while Lexington commuters come into southern Madison county and beyond as they did into Jessamine county.

All the best to you during your last semester.Househacking is one of the most common routes for new investors in NY.For best returns, I'd recommend focusing on South and Southeast Queens, Central and Southeast Brooklyn, and the Bronx.There are parts of the suburbs (Westchester and Long Island) that have househack opportunities but the property taxes are higher and the commute time to NYC is longer.Abel