Assuming you have been doing your tax returns correctly for the two rentals you already have (perhpas using a tax preparation software package), acquisition of a third rental property does not change the way you prepare your next tax return.If there is some other complexity that is the reason for your question, other than an accounting issue, maybe an attorney rather than a CPA is better suited to addressing your concerns.  

I had to have regular phone meetings with my property managers, I ended up flying to Atlanta multiple times to meet with contractors, realtors and property managers, and the amount of time that was spent looking for new deals was exhausting.

With a tax lien I am in first position, other than an IRS lien.

Certainly don't put that in a contract.If I'm selling the place, I may agree to split a % of the sale price or estimated price, this becomes more of an equity partner than an employment contract.

A dozen properties takes less than an hour per month. 

Personally I would want the security of the well planned house hack investment rather than an expensive ring but I am a practical person.

Definitely not an exhaustive list, but those are trades that I'll waste tons of time on and likely do subpar work when I can pay a pro who will do it in 10% of the time and the labor costs are pretty reasonable. 

I think a more appropriate question to get a better quote1) Instead of doors, it should be properties.If you are okay with tracking by the overall property.If you also want further tracking by unit, it would be more work and likely a larger bill.2) How many Accounts do you have(Bank Accounts, Credit Cards and mortgages)3) How many transactions do you have per account, 50 transactions will take more time/work than an 5 monthly transactions.

But with smaller chips to play with and less than an hour drive Jersey gets the job done.

One big advantage of this strategy is you can use conventional financing with a lower amount down as it will be your primary residence which also has a lower interest rate than an income property loan.On your question about buying section 8 rentals, I think this is also a good strategy to add to your portfolio and you can buy section 8 duplexes in Lansing, MI for around 100K and its a great rental and investment market.To your success!