The next move would either be to continue to pay relatively inexpensive rent and cash flow the property, creating additional income, or move into the property with almost certainty that the mortgage would be significantly cheaper than my current rent, which would increase my cash flow.What advice is out there for making this decision, how should I look at this in a unique way, and what am I not considering when making this decision?

It is a very unique property.

You're toying with the idea of paying $10K now. 

Disadvantage - maintenance having to paint every 7-10 years Vinyl:Advantage - easy to clean, durable without much maintenance (can last 25-30 years)Disadvantage - can make an otherwise unique property look cheap/generic, more expensive, hard to match if section gets destroyed I think it depends on your hold period, the house itself, and the neighboring houses.  

Maybe he inherited the properties or maybe he is in hot pursuit of an early retirement, feel him out it may open a unique opportunity or be a dead end.

I don't have a lot of cash, so I am attracted to the price range of condos vs other housing.Besides HOA, what are considerations that are unique to condos?

I’m not sure this is unique to real estate investing.

There will be unique management issues, but they are definitely more efficient investment vehicles than SFH.

@Vijaianand Thirunageswaram Given how you describe the property, then my answer would change to yes. 

When you are looking for a mentor in REI or wholesale, you have to bring a skillset or something unique to the table that can help them in exchange for their mentorship.