@Tim Swierczek is a lender and investor and can provide more a more thorough assessment.FYI, not exactly…..The “10mortgaged properties” rule for Fannie/Freddie is for Any type of mortgages on 10 properties, not just Fannie/Freddie….so portfolio, private, whatever all count toward the 10.This rule does Not apply to FHA, it doesn’t matter how many mortgaged properties you have as long as you will occupy and don’t already have an fha, you can qualify. 

your insurance co needs to know it is a rental occupied by tenants (or vacant but will be). 

How much money should we keep in savings for emergencies (I was thinking 7-10k minimum)I know the current rent on the unit occupied is $1200/month (2 bed 1 bath)I don't know what the sqft is of each unit but the total of both units combined is 1,682 sqftRight now I know the property doesn't have laundry in the units (we would be adding that to each unit)We also would want to add wall unit AC/Heating (save on monthly expenses as oil is expensive)I don't think there are separate meters for utilities (I assume utilities are included in rent?)

Found as a owner occupied first time home buyer.

I've shown occupied units both with and without the current tenants there.

Stepping up my game to multifamily…This 6 unit is rented in a decent area and has 5 rented and the owner occupying the 6th.

This is a duplex where one unit is currently occupied.

How will a lender pre-approve me for a second property that I will be occupying?

It depended on the building and how many owner occupied units they had.

He is having difficulty qualifying for conventional lending since there isn't rental history (owner occupied) and his business is often cash (unreported income).