This will allow you to compare policies, although, from my experience, most companies offer very similar coverage.As for your 2nd question, 2 things I wish I had learned early on:- Explain the benefits of renter's insurance to all tenants and prospective tenants.

If it can be categorized in multiple categories, would one benefit me more than others tax-wise? 

This way, you can continue scaling your portfolio, leveraging the benefits of owner-occupied financing while building equity in each property.It's a great way to grow your portfolio while taking advantage of favorable loan terms typically reserved for primary residences.

In most cases there is very little fix and flip profits as a long term benefit. 

Most of my clients that are doctors, typically will want to purchase real estate to not just yield the benefits of RE, but also for opening their own practice.

The short version of that is if you can buy 4 houses financed, it will make more money than 1 free and clear house;   especially when taking into consideration all the benefits that come with each house - your tenant paying down your mortgage, 3.3% depreciation on 4 houses, market appreciation on 4 houses, plus the rental income on 4 units.  

@Nicholas WhelpleyTo assess a property's potential beyond the 1% rule, consider factors like cash flow, market trends, income streams, house hacking benefits, risk management, long-term vision, and professional advice.

Not sure how much it would benefit me in the long run?

Are you looking to make cash now or reap the long term benefits of real estate investing?

It will familiarize you with the basic terminology and benefits.