I assume you would simply take the difference in rent price / the cost of those upgrades to determine if the return to do it makes sense?

At that point, start stabilizing the properties, proactively spend some cash on big ticket items (roof, furnace etc. that you know are coming due) or upgrades, then start paying them off.

-Interview realtors to find a good one and then have them meet you at the property to give you an accurate assessment of potential sales price and fixes/upgrades needed to get you to that price. 

In order to use “primary home” financing repeatedly, the new purchases would have to make sense and be upgrades from the existing duplex.

There are no large broken branches that we are neglecting.We would have to remove basically the entire tree in order to completely remove the risk of anything falling on them.

The seller/builder does offer home upgrades but trying to think outside the box instead of just taking off the price. 

Aside from the kitchen what isn't broken is out dated.

I've fairly good success with that approach.When it comes to skip tracing and cold calling/texting the most frequent mistakes can be broken down in these areas:Poor Data - speaks for itself.  

No repairs or upgrades needed.  

In summary:The place I bought from Ohio Cashflow was an old, broken down home that required frequent repairs despite having "significant" improvements at the time of purchase.