One of the first things I did was creating a Vivid Vision (Read the book) and mapping out our REI journey with long-term, short-term, and near-term goals centered around the SMART acronym (specific, measurable, attainable, Relevant, Time-based).Good Luck! 

My measuring stick was comparable rent and balance sheet. 

For me, it would help tremendously to see:Fair market rentAnnually property taxesEstimated property insuranceFair market valueOther operating expensesNet operating incomeProjected cash flowProjected cash-on-cash returnFor the record, capitalization rate ("cap rate") is a measure of a particular real estate market, so it isn't helpful for analyzing a single-family deal.

What sort of safety measures would you undergo to make sure I can execute if things go south?

I know the benchmark for multifamily is ~30%, but I haven't found any benchmarks for any of the typical RE metrics/financial measures. 1) What are typical STR expense ratios?

But seriously, working for a PM gaining experience on how rentals are managed, and experience you will gain in learning how to do maintenance for rentals and their cost are in-measurable in terms of knowledge you will experience that will benefit you for years to come.

As long as we're referring to limited resources, the tide can rise as high as you like, but there will always be people at the low end that will be unable to obtain those resources.And I don't measure my success against others.

You've got a couple different options and it sounds like the best thing to do will be measure you're ROI for each scenario:1) Put $3,500 in for touch ups and continue renting.

The Domini 400 index measures large-cap stocks with reputations for ethical business practices.

If April/May is the best season to sell a home where you are at, and you are almost done with your work, I'd say forego the expensive upgrades and aim to get it to market asap.