Quality of the Roof.  

The duplexes available in the Boston market are typically in rougher areas that come with another set of issues.If it was your first rental property, which of the three would you go with (all other things being equal - assuming they were in the same quality location).  

Come get this bad boy!

We feel it is a bad match and would rather them move out than for us to have a miserable year. 

I am hoping to skip the learning experience cost of bad PM's this time.

I own another house in a bad area next to the I275 Hwy.

the biggest issues are that the available tenant base drops dramatically around October and doesn't pick up again till the end of the school year.People are no different than animals in that regard.They want to be settled and hunkered down in a property before the school year and/or bad weather starts.Quality tenants with good financial backgrounds don't want to move their families in the middle of an icy,snowy winter for obvious reasons,and good college students have already started school in August.Many of the few available tenants will have questionable backgrounds like recent job loss,previous eviction,bad credit,difficult income verification and don't make 3 times the rent,criminal records,etc.   

Also, try your best to close on every deal you put under contract or you might start to get a bad rep in your area.As far as being a broke newbie and mailing/cold calling here is my suggestion.

Something else you may want to consider is how will this location earn you more money with a better quality of life?

Which was probably a not so bad thing considering all of the knowledge and experience I gained throughout that time period.