A wealth manager friend of mine has always said that the most savvy investors tend to make the best returns when they're going against the grain, against human nature. 

For me, I was informed about it by a local investor that I have a friendly competitive (nothing serious) nature with.  

One of the big factors in your analysis is the difference between renting this property for a premium but enduring taxes vs the tax free nature of the 1031 allowing you to leverage into two homes with a combined higher rent thus compensating for the taxes.From a 1031 perspective it is perfectly fine to sell a house immediately after you fix it - if you're intent when you bought it was to hold it for productive use.  

If it's more than 50% empty they owe you that.Also, it's about $5,000 - $6,000 to replace an oil heater with a natural gas heater.

A lot of repairs may end up causing problems with the neighbors such as the noise involved while doing the work as well as neighbors who own their units not being happy with one of them being a rental due to the general nature of renter's not having pride of ownership of their residence potentially bringing down their property value.

I am really wondering if anyone has ever dealt with properties of this nature and what their experiences have been. 

If you choose to use the direct mail route, yellow letters generally have a higher response rate than traditional postcards due to the personal natures of them.

I also have family goals that I would like to achieve, including getting my kids on the property ladder, and looking after my son with down syndrome for the rest of his natural life so that he never as to rely on the state.I have a motorbike riding buddy who has experience in real estate and who is now a mortgage broker, and so have committed to work together.So, I'm excited to be here, and have a ton to learn, but I'm looking forward to the journey.

It has no natural boundary (like Manhattan) constraining it's growth.

I currently work full time 50+ hours a week for a large Natural Foods Distributor.