@Peter Bowen Great input, i have been trying for years to pencil the numbers on a multi's to make money even close to my singles, i think one of my hold backs is my own risk tolerance/debt adversity,  and I will not do partners, so its me and my wife. i currently am  running 23% debt on $1.1MM portfolio, and have set an internal cap of 40% I know this goes against most common belief, but its what i am comfortable with.

Living in Denver is expensive, I started blowing through cash faster than I was comfortable with.

I'm not pushing you here, but if crime is low and you are comfortable walking the area talking to residents (good idea by the way), it seems like you are overly cautious looking for other reasons to kill the opportunity. 

Not many 4plexes on the market right now, I saw one yesterday that has a vacant unit but it wasn't somewhere I would feel comfortable living unfortunately.

It kind of depends on where you are in life and which strategy you feel comfortable with. 

Bottom line is that I'm still comfortable buying here but it's only at a price point that takes into account the significant repairs I know I will encounter over the long run.

I asked him what he really needs out of this deal, and he now feels that he needs at least $2,000 a month for him and his wife to live comfortably.

Whatever you decide make sure its something you're comfortable with.

I found BP about 20 months ago while looking into real estate and looking for something I felt comfortable with and hopefully be more flexible than the 9 to 5 schedule, even being able to work from home.I am currently living in NW Dallas County  and I was born and raised in the city of Dallas.  

Also have our property manager do tours of the properties and take videos on the more run down stuff so we can get an idea of how it's going.I would also suggest, once in a while, visiting any property you own with little to no notice so you can see how it actually is on a day to day and not after a PM has cleaned it up knowing you'll be there.There's no right answer of when you should or shouldn't, it'll all depend on what will make you comfortable and what you can afford.