The property next door is identical but is a single family home with two less bedrooms.  

The property next door is identical but is a single family home with two less bedrooms.

You'll be better off with an agent and PM (and contractors) that you connect with and trust to do good work than you will be in *the* market that meets every single one of your parameters.

Wanted to diversify my investments out of the market, purchase single families and see if I could make some money inside my Roth IRA.

Bought a single screen theater in a small town and flipped it a year later for 50x.

If you are just going single family then it may work, but if you're going multifamily then it may not be possible.

I invest in southside flips mostly and looking for a cheap personal living situation in one of the nice north side neighborhoods, since coach houses are sometimes pretty heavily beaten up in the nicer neighborhoods it could be a project I could afford and take off the hands of someone while giving me prime location, then eventually a rental single family unit type property when I move into something bigger. 

I will focus on small multifamily properties and single family homes in the short term and possibly trade them in Monopoly boardgame style for a larger apartment complex in the future.

I do have experience with single family homes too though.

If the mechanicals of the home (plumbing, electrical, roof, and HVAC) are all centralized to a single unit, I think your home inspector stands a much better chance of spotting an issue as opposed to a multi-unit with multiple independent systems that may or may not be accessible due to tenants.As for closing costs, try to push the closing date until you have the funds available?