That's one of the benefits w/ Carrot is we can help you cut that learning curve and make it easier and faster for you. 

For buying my first property, I really benefited from a good real estate agent and talking to as many investors as possible.

That is what you're doing - you aren't collecting the money, and you aren't benefiting from it. 

- Should I purchase the property through an LLC for potential tax benefits?

The bank will sometimes take the excess funds (difference between redemption amount and winning bid) as a immediate cash benefit on their books and write off the loan.  

In other words, the IRS will not allow you to take advantage of double tax benefits. 

They may have more flexible terms compared to traditional banks.Just be sure to check the interest rates and repayment terms since borrowing against your policy can reduce the death benefit if not paid back in time.

I hope you have looked into the cost segregation benefit of STRs.

Please any advice on my ideas or changes that may benefit them would be greatly appreciated and I appreciate the time you took to read this.

Sometimes you buy low, sometimes you buy high.But as long as you stay in the market, you benefit from the tendency of the market to go up over time.People think of buying a house as this one time thing, but it’s actually more likely that you will buy, sell, refinance a few times over the course of 30 to 60 years.