For property tax reasons, these lots were tax assessed at no less than $5,000.To put this in perspective in today’s dollars (this was 40+ years ago) he would have paid maybe $500 for a tract of land tax value of $35,000.  

Account Closedi am happy to share some perspective.  

I do understand everyone's perspective.

There's probably no "do this" and it works for everyone so keep gathering different opinions.The way I view a "good deal" might be different than how you view a "good deal"...so let's look at it from an "average" person's perspective.  

Alec,From an Insurance perspective, ask the current owner to get from their agent "Loss Runs" for the past 5 years.  

For perspective, the house directly next to this house is estimated at over $900k fully updated with slightly higher square footage, but 1 less bedroom.

You can probably make it work, but need pretty active management and long term perspective on it and you should weigh if it's worth your time and effort. 

I would like to hear other's perspective on this topic.

Pain points that I'm not yet aware of in this space, that I can potentially approach differently/with a new perspective.

I appreciate your perspective (e.g.