When I move out I plan to cashflow only $150 a month which would be the cashflow after hiring out a management company and after paying for repairs and Capex.

In such a situation, it is advisable to hire a professional property manager to manage the property for you.

It will in no way increase your tax liability, but it could be an audit flag for people not paying taxes on rental income.Also be aware as a landlord, if you hire services and pay someone more than $600 a year, you are required to send them a 1099 and file with the IRS.

I am most interested in purchasing a single-family home in Orlando as a long-term buy-and-hold investment property.For the rental strategy, I would like to rent out the home by room instead of renting out the whole property to one tenant.I am located out of the country (in Dubai), so I will need to hire a property management company to take care of the home for me.  

But just look at how much Van Life has blown up among people who are freelancers/working remote!

If this is the case, you should hire a Property Manangement company to do that for you!

Me having extensive background in waterproofing I ended up just doing it as it only costs me actual costs not the costs of hiring a contractor.

Is there any occasion you regretted not hiring professionals for a specific task/service?

If you just hire the cheapest or first PMC you speak with and it turns into a bad experience, please don’t assume ALL PMC’s are bad and start trashing PMC’s in general.

Buying 7,000 homes isn't difficult if you hire 2,000 people to do it and pay more than the house is worth.