For me, if I make $1500 net per month on a free and clear property I would make $18,000 / year.  

If you haven't already, read "The Book on Estimating Rehab Costs" by J.

You can also assess a dollar amount that you value the cost of these requests to be, and ask for these as a discount from the purchase price or a concession to you for closing costs. 

Again I cannot collect rent to justify this cost/effort.  

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

We'd spend about 2 weeks delivering all the bundles and I was the "free" labor until I finally negotiated 10 cents a bundle from my old man.  

Not going to give here a lecture on S-corps, but take my word: no benefits, only extra hassle and extra cost, such as preparing another tax return.

I own the property free and clear and i use the equity as part of my business line of credit.

Propose starting small, like a single-family rental or house hack, with a clear, low-risk plan to minimize concerns.Leverage your industry connections and offer to handle the initial responsibilities, demonstrating your commitment and capability.

Feel free to reach out and we can discuss.