Have you found more expensive insurance is simply "the nature of the beast", or is there a better way my broker and I can go about keeping costs down on that side?

I'd encourage you personally to either consider a strategy that allows you to add value quickly and get out quickly (a Flip or BRRRR) if the HELOC is your current only/best option for cash, and/or to simply save up.

I simply call my broker and add the customers name to my liability policy.

If you do not close on enough of your properties to defer all tax you will simply pay the same tax you would have at the same time you would have.

Don't give names or addresses, but simply ask hypothetically. 

Seems to me whatever % you would give up would be offset by simply renting out the upstairs unit.    

In your case, I would simply point out that they forgot to give a value for that space.

I’ve heard from some investors that are perfectly okay with simply breaking even on rental properties in the current market, but I’ve never had the risk tolerance for that.

I've learned over the years that real estate investment is simply a math problem.

Imagine you bought a property for $2M.The land (excluding any structures) is valued at $400K.Since land is not depreciable in the eyes of the IRS, we subtract the land value from your purchase price to get your depreciable basis.Your depreciable basis is simply where a cost seg engineer starts from when allocating your eligible assets into either 5, 7, or 15 year property.In the scenario above, your starting basis would be $1.6M since your basis = your purchase price - the land value.Having an accurate land value is essential to getting your depreciation/bonus depreciation calculations right.This is the starting point for any cost seg study that you do.