Let me address your questions and provide insight from a lender's perspective:1.

Though USLI, one of the biggest umbrella policy providers, dropped my max coverage to $1M because I had pools.

You should also check to ensure they have Errors & Omissions insurance, Fidelity Bond coverage, and a Financial Institution Blanket Bond.Some are more consultative and advisory and provide guidance, while others are just processors. 

Looks like Tim and Ezekiel have provided a bunch already...What are costs associated with snow/harsh winters?

Didn't they provide you with the guidance on how to open bank account for the LLC?

The information you provided is very helpful. 

They provide flexibility and efficiency, especially for experienced investors.How have you found the terms and structure compared to traditional options?

A good realtor will have all the revenue and provide whatever is needed to make a sound decision.

STR can provide more cash (potentially), but its a high risk high reward strategy - if you invest in the furniture, staging, photos, and management or self manage, there is a lot of time and money invested.

I am just looking at numbers provided by Zillow.I agree that the cost for most items such as a Roof, HVAC, Piping will be similar between a cheap home and an expensive home.