So my question (which could have been clearer) is less about tax burdens and more of an ethical one of: which party should the tax payment originate from?

The PAL rules deal with "activities" and the taxpayer's level of participation in said activities. 

Taxpayer Advocate Services are a taxpayer funded group that are supposed to be the "watchdog" that helps taxpayers deal with these types of issues with the IRS. 

It's the delay of tax payments only.

Calculator should provide amount of conversion  tax payments needed, one or multiple conversion options,  Medicare IRMAA impacts, various investment percentages of Roth growth vs IRA growth, and RMD amounts with associated tax bill.I’ve seen numerous CFPs hawk their services for $5,000 or more.  

As the local governments struggle to manage tax payer money responsibly, they should really offer incentives to private builders to build "income restricted" at a much lower price. $220-$300/ft for vertical build costs.  

The IRS imposes a 20% penalty for inaccuracy when a taxpayer significantly overstates expenses. 

So it is a different tax payer. 

According to IRS Rule That means at least one of the following is true:The taxpayer works 500 or more hours in the business during the year.· The taxpayer does the majority of the work in the business.· The taxpayer works more than 100 hours in the business during the year, and no other staff works more hours than the taxpayer.Hiring a property management company, therefore, effectively off-loads the primary work from the landlord, allowing for the income generated by the investment to remain passive and lower tax rates than active income.

@Thomas Talbert your CPA should be telling you that you need to make yourself a W-2 employee of the company and pay yourself a monthly paycheck.The payroll tax deductions will help avoid a huge end of the year tax bill.Also, too large of a tax bill will piss off the IRS and they may charge you penalties + interest for not making quarterly estimated tax payments.