While the prices are attractive, I'm concerned with its long term viability.

This approach does not work on every deal, but if they are doing 1 out of 3-5 deals like this, it really helps the fix & flipper to develop long term wealth, rather than just chasing the next deal for chunks of money. 

There is a single family home that was divided and one half has been rented and an ad on small "house" that has also been rented mostly long term.

If one tenant has been in there for that long, there will also be some serious capex and turnover costs.

I wouldn't imaging the state where the entity is registered makes a big difference for most buying and selling purposes as long as you can provide all of the required documents for title purposes.

My only question is what took me so long to hire the bookkeeper?

I have an opportunity to make a quick 30k in equity, but only cash flow around $25 — if I look at long term appreciation, that seems to make sense to me, but am I overlooking something and trying to make this work?

With that said, the income can still offset the cost of holding the property as a long-term investment.

The strategy there is more about long-term appreciation since cash flow can be razor-thin.

Now he has sold the company and is more of a flat rate charge based loosely on how long it takes him to prepare the return.