You could try to find something that needs some either minor or major fixing up, and adjust your budget lower to account for 50-100k in renovations, or start searching for a lender that can help you with the construction costs, and then pay it off once the renovations are complete with a refi.

Several methods come to mind for the ADU.   1) a regular or periodically adjusted flat fee (based on an estimated usage); 2) factored into the rent (essentially the same as a flat fee); 3) percentage proportionally based on sqft. 

As for feeling like it's too much, you could review your policy with your insurance provider to see if there are any adjustments you can make to better suit your needs and budget.

Tax RepercussionsKeep in mind that every real estate market is different, so you need to adjust your strategy to the particular circumstances of the region you are investing in.

Your adjusted returns would be higher because you're saving $700/month on your housing expense.

If the OZ is held 10 years the basis is adjusted to fair market value upon sale. 

Growing, Maintaining, looking to adjust to maintain returns, Looking to reduce risk....These two voices will steer you to the geography and type of real estate best for you. 

For our planning clients we use software where you can link all of your accounts and manually enter too, and so it operates initially like Mint but goes way further with great analysis in all core areas, particularly taxes.  

Eventually, you begin to develop  detachment as a survival mechanism.Some people find it really easy for others it is an adjustment to work in this space and see the reality.  

I like what you mentioned about adjusting my budget to accommodate for 5 touches.