The experience was really bad as I was getting 1-2 year old leads to cold call that I knew had a 0% success rate and I do much better generating leads organically on my own.

When you live in that duplex for 2 years and then sell you'll be able to take 50% of the profit tax free (the allocation for the side you lived in). 

To get things done as quick as possible , charging by the hour cost the contractor money , charging by the push/inch  is the most profitable way to do snow . 

Should I buy it and take  500-600 less profit per month knowing I can sell it for a large profit as is or even more if completely remodeled?

Like @Kyle Mccaw noted there is significant value in goodwill and I imagine you profited nicely over this pleasant long term relationship. 

If both houses were sold in 2024 then the loss will negate the profit from my understanding.

It's not just the taxes, but being able to at-a-glance look at expenses by the month and year, profit and loss calculating automatically, and even cash flow by property and total portfolio by month and year.Thanks for suggesting it!

You could organize your own in-person event and market to your avatar. 

The $10,000 yearly maintenance fee is really hurting your cash flow, as it’s eating up all your profits.

Make it a habit—underwrite one deal a day until you get the hang of it.The tougher part, and I think what you’re really asking, is how to turn solid underwriting into a profitable deal.