You don't want to lose your rate on the house you are living in now unless you want to sell it so since that is an owner-occupied, you need to stay there and save up the 20 percent for the second property based on what you said.

The agencies require all properties be - on average - 90% occupied over the prior 90 days (IE - the property needs to be 90% occupied on average over the trailing 3-months leading into quote / commitment).

Because 0-5% down does NOT happen unless you are owner occupying the home.

We have taken over LOTS of occupied units with under paying tenants.

You're only limited by your beliefs.Practically speaking though, 2-4 unit multi is very very doable starting out, especially if you are willing to owner occupy.

I'm beginning to renovate a multi family unit on the southside of Chicago that has been occupied since being purchased (9 years ago.) 

Other than that it's a pretty clean package. 200k down, 720+, 60> ltv owner occupied.  

Hello Dana, For that purchase price in Brooklyn, NY, you could be looking at considerable unknown expenses at this point.If the property is occupied, you'll have to factor in attorney fees and holding costs while you wait to gain access to the property.Furthermore, you could be facing additional costs related to title issues: open permits, violations, liens, judgements, etc.

Because the property tax as a non-owner occupied property is about 3-4 times the amount of a owner occupied property.  

If you had also spend money on renovations and improvements while occupying those should have gone into service then as well.