I haven't reviewed the Standard Lease Agreement yet, but all I need is the right to sublet, and possibly some negotiated capital responsibilities (owner pays for repairs over a certain amount or split responsibilities on certain expenses).

The plumber’s report indicates that the leak may have been caused by an overflowing tub or sink upstairs, but the tenant in that bedroom denies any such incident.As a result, I now have substantial expenses for the plumber and restoration company, including drywall repairs, painting, texturing, and reinstalling electricals.

The lost rent was the biggest expense at 14, 400.

I made cash only payments and use envelops to measure my expenses. 

Make sure you've got cash reserves for closing costs (around 2-5% of the purchase price, repairs and maintenance (aim for 1-2% of property value annually), vacancy periods (budget for 3-5 months of expenses), property management (if you're not self-managing), emergency funds for unexpected repairs.When choosing markets, look for those with stable job markets, growing population, and strong rental demand.

I've been doing a deep dive looking at cash on cash return for various down payments and expenses on properties with a mortgage.

It's all the expenses minus financing. :) 

House hacking can also be a solid way to offset expenses early on.It sounds like you're diving in with a great mindset and skill set—being handy and managing yourself puts you ahead of the game. 

Then with the more expensive homes, you leverage.

Question is, if I have the means to put a high enough down payment on a house to be cash flow positive (assuming my expense estimates are accurate, etc.) is that something that I should do?