You will learn a lot on your own home that will save you time and money on investment property.

Tax Savings with Cost Segregation: With a $2M property, cost segregation allows $316k depreciation in year one instead of $28k.

We plan to stay in this house for more than 5 years unless another great opportunity arises, but maybe it is best to allocate a bigger portion of savings to our real estate investment savings account than our home improvement savings account for the first few years.

Is saving the fee a PM charges worth the potential thousands in cost and headaches?

The use the rest of the money from the sale, plus the interest that you've earned off of that money plus the money you saved in rent by having the tenant in the other side make the mortgage payments. 

Ultimately I agree that responsiveness is very much appreciated, but you won't really know that until you start working together with the agent.

My ultimate goal is to house-hack this deal as well. 

It is a tough market and there's nothing wrong with taking a breather and waiting for things to stabilize while focusing on savings and education.

Operationally, it's easier in multifamily and you'll have cost-saving opportunities as well when it comes to certain expenses.

I have a W-2 Job, capital saved up for a down payment (or two), and a buy box based on my affordability.