It's not just about ease of bookkeeping; it's also about legal protection.

I am using Quicken Rental Property Manager for my rental property bookkeeping as well as all my other personal finance needs.

With a HH, you can learn how to analyze properties & markets, how to find an investor-friendly agent, how to spot value-add opportunities at properties, how to engage in a strong due diligence process, how to screen tenants, how to manage the property, how to build a network of contractors, plumbers, electricians and other pros, how to manage the book keeping of the property, etc., etc., etc.

(1) Email response templates to applicants in marketing funnel.(2) Notice templates to tenants (notices to cure, 3 day, "reminder" violation letters).(3) Rent collection only via tenant deposit into my bank accounts; email alerts for deposits for bookkeeping on my end.(4) Exterior maps and instructions for lawn service and snow removal, since I go through those contractors like **** through a goose.

A good one can help with the following:* Helping to organize a bookkeeping system to ensure no obvious deductions are falling through the cracks* Providing guidance on entity selection* Developing a tax strategy that is custom made* Filing compliant tax returns* Etc, etc, etc

Some of the activities that count towards your hourly requirements include collecting rent, bookkeeping, advertising, maintaining legal compliance, safety reviews, inspections, decorating, tenant approval, contractor supervision, procuring insurance, paying taxes, and actual hands-on maintenance.There are some activities that do not count.Travel: While you can deduct mileage and expenses for your travels to and from your rentals, the time spent traveling is considering commuting and therefore does not count towards your hourly thresholds.

I offshore PM, bookkeeping, interior design, etc.In Quickbooks, for example, you can add someone as a bookkeeper so they can reconcile your accounts but they can’t access payroll, etc.

Can you find a deal and market in that 5 hours where you make over 1000 or 10000 vs doing bookkeeping where you are paying someone few dollars? 

The actual bookkeeping file would be even better. 

At about 20 units you need to start outsourcing tasks, but I would keep it all 1099 and divide different tasks to different people, contrators, handyman, bookkeeper, and admin.