My issue that I’m having trouble getting over is that down payment money is currently yielding 5.5% in an HYSA with no risk or stress.

We are all human and make mistakes.Yes, you will have the same issues when you go to sell it.Good Investing...

That's a nonconforming property, where you have fewer lenders that will bite on it so you are limited there but let's assume that's not an issue. 

Technically on paper I do not own this property, however we are putting the property into a land trust that we will both own together 50/50.In speaking with a couple attorneys, I am getting mixed answers.

If you discover foundation or structural issues these can also be expensive.I would not use a per square foot figure like, $50.00 or $75.00 per square multiplied by the number of sq. feet.

If you sell now its a 15-25k loss unless you do FSBO, then the loss is smaller.If you don't sell you may be negative around 4-6k each year depending on the capex timeline/maintenance issues.

From June until November I haven't received one payment, my court date was set on the Monday of Thanksgiving which the clerk couldn't give issue the court order document because she was swarmed with all the cases that week, the following week I received the court order and the writ.

But this is not the issue.

The tenant from the unit with the leak supposedly moved out because the leak issue was not being fixed.

Ideally one with insurance to cover any issues. 2.