Plus if you bought with all cash from the proceeds of the sale you would be trading down in asset value quite a bit.Depending on the refi rate you could consider keeping this and refinancing it to pull some cash out which you could use as a down payment on another property.Just some thoughts, hope they help the issue with the refi is those rates at the new loan if i do a 75% LTV will almost overcome the cash flow its producing now and basically get to a break even point.

If you have a lot of equity in your home I would first evaluate if it's possible to leverage any of that equity to acquire another asset that would produce more cash using a home equity loan or line of credit3.

Very likely the seller doesn't know the income-producing value of those extra spaces and therefore has not included it in their pricing.

If $23k is just a “hope and a prayer” then he’s going to have a very hard time producing any CREDIBLE itemized bill.  

You may see a difference if you're selling to an investor that would price it as an income producing property. 

The C areas that produce the most cash flow are Linden, Whitehall, and Hilltop.

Rental estimates as in what it could possibly produce?

They'll produce a title commitment with the requirements they think are necessary to get you insurable title.

If it is way more work and maintenance but cash flowing the same as a smaller unit doesn't make sense, but since you say high maintenance high reward I'm guessing this is one of the best producing properties.  

This comes with time and experience but a book that helped me tremendously (not really a sales book, though) was "Boundaries" by Henry Cloud.The most common challenges for RE Agents early relate to generating leads and focusing on income producing activity.I would consider spending 50-75% of your side-hustle time on income generating activities.