Just do what is average and do not cut any corners. 

My goal is to find a property that my family (myself, wife, and two babies) can house hack to cut down on our living expenses (obviously). 

With crowdstreet you are InvestIng dIrectly wIth the sponsor so there is no middleman to take a cut so the returns I have found to be much better.

Dealing with lead paint is one particular thing I have seen first time flipper totally miss and see them taking short cuts that eventually come back to bite them.

Suddenly the tree shading their windows is cut down, there are leaf blowers going at 7 am on the weekends, water shut offs 'for maintenance', etc.The issue here is that whatever his play is (and it doesn't matter what it is), you are along for the ride because your only remedy is lawsuits if he's not playing ball. 

I still have my due diligence cut out for me, but I'm considering investing in a rental property in Miami.

Having them on a 15 year product is cutting the cash flow significantly, but would allow me to pay them off sooner. 

This will cut down on minimum required distributions when your 70 1/2. 

Pay the extra for someone that won't cut corners.

Your best option is to hire a reportable lawn care company and increase the rent to cover the fee.We assign snow removal, grass cutting and keeping of the gardens within of our leases.