We are looking to outsource this part of our marketing and need some advice.  

I'm looking for someone to help with data analytics, quickbooks reconciling and such, CRM management, transaction coordination, and basically any other task I can outsource. 

Lead generation is th elifeline of your company, anyone that outsources lead gen is  friggin insane and deserve to fail.

Luckily, so far everyone I've talked with at City of Portland has been gracious with me being an amateur asking questions and instead of a conventional route for the site plan / architectural drawings I'm at least starting out with outsourcing it to an architect in Pakistan (and then adapting the lumia drawings myself).

I'm big on outsourcing at this point in my investing career.

You can have a tenant take care of the lawn care and give them a rent reduction of $15 a month  But I would outsource the snow removal and snow care to a reliable professional person that is insured.  

You could also start outsourcing the backend office stuff to remote workers for under $10/hour.If you have trusted contractors, the remote workers can also run 80% of maintenance.

Additionally, when doing calculations, I always like to add in property management even if I am going to manage it myself because in the future, you may want to outsource that to someone else as you get bigger, so would be good to factor in.

For example short term rentals are good for immediate cash flow but unless you want to outsource it and pay really high management fees, managing short term rentals will typically take more of your time every week.

If you want to outsource, then be loyal to your property manager.