With sites like Airbnb, VRBO, Homeaway and the like, it's never been easier to keep these units occupied and make great returns if you or the right property management company can manage it optimally. 

Focus on getting started rather than hyper-optimizing for the best possible scenario in the short term.  

We haven't had much experience with the taxes involved with rental properties, but are trying to optimize our potential deductions.

In more specific terms, you need to figure out what the optimal DTR is and meet or exceed that if you want to be in a good position for loan.

Additionally, there is so much waste through a real estate transaction, it will take a long time to fully optimize the process (brokers, lawyers, title companies, appraisers, inspectors, they all have areas which can be optimized) I’m a licensed broker in NJ FYI

The fact that someone is newer to the process or less experienced will likely (but not always) lead to a less than optimal return in the first place.

In those cases, you are optimizing for return AND stability.

To optimize a BRRRR I specifically look to add additional livable sq ft.

dl=0  Previous property owner was in an estate (the tenants parents died), the tenant is living there now and my realtor and I spoke with him and he's agreed to move out (cash for keys) in ~2 weeks- figured this was more optimal than having him potentially unruly, and starting an eviction process. 

If you convert to a policy optimized for cash value, you'll be trading death benefit for cash value.