Obviously would be a slower process, but would create very little debt hanging over your head.

Is it foolish to consider using the HELOC for the down payment?

He gives me a $20,000 down payment, and he will owe me $180k, making monthly payments for the next 20 years.

Hey Tod, I took a very brief look at your first listing, airbnb.com/h/newport1bedroom, and the thing that jumps out at me as far as improving it is: address the 1-star review head on without attacking the reviewer.

If your agent can wrap their head around this you might want to look for new representation.Good luck! 

Try to put a bigger down payment in than you might need to give yourself some breathing room.2.

I wanted to invest where I wanted to live and I am also from Elgin so am constantly headed further nw. 

He then proceed go down $50k on their original offering to me because of the scope, amount of money, and my (apparently) my newfound lack of “experience”.

You hit the nail on the head...that's where the SFH to Duplex conversion gets financially unrealistic.

Thanks for readingDavid I would not buy anything right now, I would wait a year or so and see where prices are headed.