There are a lot of good things about Wyoming LLCs, but the favorable Wyoming laws don't matter as much because the state you are in will apply the laws of the state the property is located in. 

Compare other rentals with a similar size, location and bedroom count to get an estimate of what the rent would be while you're living there.

This might be a question for our insurance broker/future attorney, but wouldn't the LLC be formed in Indiana since the rental property is located there (versus Illinois where we will be living)?

Maybe I should join a meetup for another location?

Good luck on your journey and I hope you provide the financial security you hope for to your daughters. 

@Seidy Lasker Wash sale rules apply to stock options if they are deemed "substantially identical" to a security sold at a loss within 30 days, such as options with similar expiration dates or strike prices.

I would imagine most attorneys located around the MA, NH border area plan to make more than $200,000 per year.

Northern and central NJ are preferred as I am located in Bergen county.

I See your located close to where I am in Florida.

The terms and costs will depend on the property, your personal situation, the location, etc.