And then you also calculate the cosmetic upgrades given. $800 / unit?

Plan is to upgrade them as they turn over increasing gross rent from $2000 to $3000-3200.

Sure you could do the 1031 exchange into the next property, but that's usually to "upgrade".  

Current rents: $2450 which I would plan to raise to at least $2900 ($1400 and $1500 for second unit which has some upgrades.)

It has fallen victim to a few of the typical things in the area (windows broken, damaged door, etc.)

The owner is the daughter of the couple who past and they want 195,000 it has 2br,2bath full basement,fenced yard needs no work but kitchen and bath could definitely use upgrades but could definitely be a turn key or rental seems like a no a no brainer however comparables in the area are 149 to 173 and those have full remodels done and most have 3br there about 30% above price on zillow(i know thats just an estimate) the one thing that really stands out is that the house is directly behind the train tracks so location is whats causing the home to be not sold with that high price any advice to help me close this would be fantastic thank you 

While the numbers look awesome there, you have to take into account crime, unwillingness of contractors to go to certain areas (their trucks/vans get broken into during the daytime even and tools aren't cheap). 

Am wondering how to start working on my next deal now that I'm finished with renovations/upgrades on my current property but it isn't yet on market.

I did find an article with someone in a similar situation though who owned a one bth, one bd condo and then upgrade to a 2/1.

It needs a new roof on each building and there are lots of broken/plastic windows.