The first thing here would be the regulations and laws governing acquiring properties, managing properties and selling properties.

I manage quite a few properties in those markets.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Looks like most every other all in one management tool.

You may want to make an introduction between your CPA to those 2 colleagues.The CPA can go over their services and pricing to your colleagues.I partner with many people on real estate deals - It never gets to a discussion on whether they do their own tax return or hire a professional.If a partner mentions he will provide capital - does he provide the capital on a timely manner.If a partner mentions he will find deals - does he find many deals and provide an analysisIf a partner mentions he will manage a property - does he manage the property well(find tenants, collect rent, communicate with contractors, etc)

I manage around 400 rentals with 14 years of experience and have never been sued once.

Keep systems in place for managing documents and contracts.6.

Try interviewing at least three managers.1.

Don't change jobs or income yet.Once you do and you think you can manage the payments based on your new income, maybe once you get the rooms rented.Then if you want to switch there are plenty of opportunities. 

Managing a rental (even if it cash flows) comes with responsibilities, and it might not be worth it for $300 a month.