You can find positive cash flow in both markets. 

Now I'm wondering if I should re-strategize.

Its always nice to hear positive things about local people. 

If the place is vacant, you are still taking that money out of your own pocket.I don't disagree with having a strong cash position; most of my properties are f&c.

The triplex is occupied and currently bringing in positive cash flow.

There is now some positive cash flow (not much considering the value of the asset, but a lot considering where the initial cash flow was).  

And start from a position of strength rather than getting into a property right before you go back to finish up school and have no income for a year.

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

Those positions are hard to come by but if you can find one and get your green card, you're set! 

The cost to build will be significantly more than the amount of “value add” of an ADU putting you in a negative equity position.