I then hired contractors for plumbing, electrical, roofing, and HVAC upgrades.

We have hired   a property management company for all three rentals.

I recently hired them to clean up my credit with the intention to take a serious look into the MAP program.

Work out a fair revenue-sharing model, such as a flat lease or percentage of profits, and consider hiring a property manager for oversight.This post does not create a CPA-Client relationship.

Consider hiring a Property Manager to manage out of state properties.

Tools like QuickBooks or even a simple spreadsheet can help you mentain compliance and prepare for audits.Reinvest WiselyScaling a short-term rental business often requires reinvestment in marketing, property upgrades, or even hiring help.

Here is a link to 100+ bartending jobs currently hiring in Toronto. 

These expenses can create a paper loss, which may offset other passive income or carry forward to future years.If you qualify for Real Estate Professional Status (REPS) or actively manage a Short-Term Rental (STR), the losses can be applied against your active W-2 or business income, reducing your overall tax liability.

You'll probably get better service approaching it that way than hiring a professional manager anyway.  

.- Once your time is more impotant to you then the cost of a PMC, you can hire one.2) Hire a PMC to guide you on your first rental and learn from their expertise.- You can buy additional properties and DIY manage those, perhaps leaning on the PMC for any issues you're not sure how to handle on your own.Good luck:)