I am looking to buy a 2 or 3-unit home in NYC. I plan on renting a unit and probably getting a roommate or two in my unit to maximize cash flow early on. So far, the best deal I have been able to find is 5% down with ...

Air coverage can require your primary insurance to pay out first.

There are about 20 companies that do this and more or less take over as the primary lien holder in place of the taxing authority. 

It is so much easier to get a HELOC or second mortgage on a primary residence, and much more difficult and expensive to get one on a rental house. 

Hey Brandon, Some would require some reserves, or at least to show cash to close on any new deal.Are you anticipating opening up a HELOC on your primary to get the cash needed to close? 

If you are purchasing a primary home, income could be a challenge if you work at an office.

There are several myths that we have to debunk before someone truly believes they can do it.You need millions of dollars to do a dealThat it’s too complicated to figure outThat permitting takes yearsIn those communities developments cost way less (think a couple hundred thousand along with a loan from a regional bank), permitting is not difficult (much less red tape), and the towns are small enough that both the city staff and the local architects and engineers and contractors all work with you to help you navigate the process since you’re all invested in making your community better.Note: The big boys can play in the primary & secondary markets.

That being said, I had competing issues. 1) my wife and I are buying a new primary residence (much to my chagrin), and 2) in december, we bought a condo rental that is currently being renovated (a much lighter project) and that process is also a little stressful.   

Paying down debt on my primary rez does not make progress toward those goals.

Since you and your partner are unmarried and own a primary residence together, tax treatment of deductions (e.g., mortgage interest and property taxes) requires careful allocation.