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 . 

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

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?

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

The first year we spent $45,000 on the program, and our deal flow doubled with our net profit up 70 + %.  

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!

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.

A mortgage lender can help determine if refinancing or tapping into equity might allow you to acquire additional properties.Consider a 1031 Exchange: If you're open to selling a current property, a 1031 exchange can defer capital gains taxes while enabling you to upgrade to a larger or more profitable asset.

Additionally, keep in mind if you do this in a Roth then there are NO taxes on the appreciation, rental income or profits when the Roth liquidates the asset.