@Justin Eaton Nice!

I am looking in Massachusetts so we have a lot of older properties, some of which are redone and look very nice and rentable but I worry about dealing with maintenance issues that come with older properties.

I already have a nice sized emergency fund for repairs and such, and 'm working on negotiating the price down some more so there's still wiggle room.

If I move and decide to build a fantastic, very nice duplex then yes I might use it, but first I would have to convince my wife to move out of home she really loves......probably won't happen.  

"You are nicer than I am" Not nice, naïve.

It's great that you have a nice plot on hand and are capable of managing the projects yourself.  

Using streetview, Havenwoods looks  a little older but okay, whereas the street/adjacent streets for the Lincoln Park property I'm looking at looks pretty nice. 

it's a distressed property so of course there are some things wrong.it's freddie mac REO, way past the owner occupant period which ended in january 2018. it was originally listed at 50k dec 2017. went under contract in july at 42k, now it came back at 38k. but looking on redfin it was on and off the market since 2012.its in a neighborhood where houses are selling between 70k - 135k. in fact the 135k looks just like this one and its on the same street. on the inside it's pretty nice, seems like just paint and flooring. might need new mechanicals etc and some mold in basement. so as a newbie i'm thinking, what am i missing?

house hacking may not work for us due to need for at least 4 bedrooms.  

Ok the scenario.Recently closed on an investment townhome with a nicely landscaped back patio.......a small but clean little trek deck and some nice pavers that created an attractive useable space.