I've hired social media experts (a little different) that work under a similar structure and it's been working great.Not to mention team off-sites if you guys are located in the same area also help a ton.

Utilities will be an issue.  

Most landlords wait for a problem to land in their lap, then they waste a ton of time thinking, worrying, researching, and bleeding money before they ever take action.

Not to mention they wrote of over $300k worth of taxes for me utilizing a cost segregation study. 

We couldn't help but improve the houses a ton, and part of us feels like it's a 'waste' to just have them rented, as it will put wear and tear on them until we do want to sell

Quote from @Ashley Kehr: There are a ton out there, but if you are starting out to mid level I like buildium.

My basic underwriting making some standard assumptions on HOA expenses, 20% down, 7% interest rate, 30 year mortgage, utilities, supplies, and maintenance costs shows a loss of about $22k per year if you are self managing.

- Usually a 5 unit with a boiler means that all the units share the boiler heating system.Which specific utilities in which units are paid by tenants vs shared?

I'd be surprised if the complex doesn't have individually metered units so you may be able to eliminate the utility expenses unless those are for common areas like walk ways, parking lot or laundry.

That's three months of mortgage and utilities, the cost of flooring, and the cost of painting.