After spending countless hours answering numerous questions and being on hold with numerous insurance companies and brokers, I have had two refuse me at the last minute just as I was about to sign up.

I know that they aren't helpful as a metric-- trying to regress a complex situation down to a numeric score usually isn't helpful-- but in what ways specifically do they fall short?

Like @Brandon Turner has mentioned numerous times in podcasts /webinars, start analyzing to see whats out there.

This was my first year investing in real estate and I purchased two properties (a duplex and a single- family that I house-hack) read numerous books, listened to dozens of podcasts, and met a number of successful investors through real estate meet-ups.

Fantastic explanation!

What they can help you with is options for types of accounts you may be eligible for, and an explanation on how they differ from each other (rules, regulations, contribution limits).

I started my real estate learning about 2 months ago and though I'm about a year from buying my first deal at this point I have talked to mentors, read numerous forum posts, and books and have made a more concrete plan.

She has received numerous offers over listing price ($510k), but every offer requires it to be delivered vacant.

But I'm having trouble following your explanation.

I have contested my property taxes on numerous occasions and have not had as much luck as you.