If it is for tax reasons, calculate your depreciation and consider a cost segregation analysis to maximize the deductions.

While I wouldn't call it "big boys" - there is a very small world of professional companies dedicated to this super small specific asset class. 

Instead, go get an umbrella policy on your homeowners insurance for protection, and you can deduct the exact same expenses on your personal tax return as you can with a LLC.

A lot of times, these types of lifestyle choices will start limiting you down very quickly to specific areas, and since you are going to be living in the property, are likely to have a heavy weight on the neighborhoods.  

I guess were not sure the best route to take and specifically how to take it.

What specific steps should a new investor take to make sure distress is only cosmetic and not structural if we have no construction background?

Anything specific in your plan or locality that would force this?

I know you will find a ton of encouraging and helpful people here.Regarding HELOC I suggest you connect with my good friend @Michael Barbari...I believe they can still do up to 90% which is 10% more than most banks.If you need any other specific connections here in Chicago I am happy to provide them. 

For your first unit, unless hiring outside management which means giving up 20% of earnings, you're going to have quite a hurdle to operate a place remotely.I don't necessarily think looking at market specific data around the country and thinking you can just dive into that market and do well makes much sense.

I understand what motivated sellers are and when you do, you will see that you CAN NOT target them.So I focus all my energy into being the easiest person ALIVE to be found to a very specific audience: People that are willing to sell their house below market value".THAT is how and why my wholesale deals reach 6-figures+ consistently.Want more direction?