Your inspector should give you a good idea if there's anything big and pressing.Also, if you house-hack, that hopefully means you'll pay a lot less in your mortgage than you're currently paying in rent?

How many months reserves for mortgage payments do you reccomend? 

The units without mortgages typically net $10-12k annually and the units with mortgages net about 1/2 that.

My mortgage has been approved saying that it would be owner-occupied though my broker told me there is no real consequence of just not living there once it's already been approved.

These lenders often have more experience and flexibility with properties that include ADUs and JADUs.Community Banks and Credit Unions: Local community banks and credit unions may be more willing to work with you, especially if they have a better understanding of the local real estate market and the value ADUs and JADUs bring to a property.Mortgage Brokers: A mortgage broker may have access to a wider range of lending options and could help you find a lender willing to consider your property.

Is it possible to actually have your roommate paying most of your mortgage in an expensive city like NYC, via house hacking?

Recognize the fundamentals of private lending, mortgages, and innovative financial techniques.

Small private rd to access the property.

We rent out our previous home and bring in $600 a month on it after mortgage, taxes, and insurance, but she doesn't see it as an investment property and so it has been hard to continue investing without her support.

But your mortgage will stay the same.