If rates are similar, option 2 would allow me to increase the potential number of deals while decreasing complexity. 

My wife and I are currently buy and hold investors in Northern New Jersey but we are exploring the possibility of moving back to my wife's home city of Portland, OR within a year to 2 year timeframe.We are interested in spending a day viewing multi-family / apartments complexes.

noone will finance you an apt building unless you have the experience of running a SFR or a duplex. so start there unless you have lots of money and just want to buy an apt complex for the hell of it.

I would agree with @Nicolas Paez that your expense estimates are way too low for such a neglected complex.

This will leave you with 200K (10x20K) (I won't consider tax for this example).Of this 200K, take 150K and buy a 600K apartments complex (let's say a 8 units since I don't know your market).Put 150K down and finance the rest with a commercial loan for 450K. 

Very expensive mortgage, but could use the income from property(s) to qualify for re-finance conventional in 2-4+ years depending on property type.Property options, potentially a mix of a couple:* Large 8-20 unit apartment complex(s) $500k-$1.1ish - Local or long distance.* 10+ "turn key" Harrisburg, Pa houses @ $60k - $125k* 1 or 2 new development townhouse in an upcoming RiNo area of denver for ~$450k, with the hopes of appreciation in 5 - 7.5 years and sell.

Lucero - I'm shooting for 4-5 SFHs and a multy-family/Apt complex.  

Multifamily is a complex game that most newcomers underestimate, oftentimes to their own peril.  

I'm going to be looking for an investor for a large condo package (40 units, same complex) and I need help negotiating/analyzing the deal in order to make sure it's profitable and attractive for an investor. 

They don't want to live in loud, busy complexes.