@Luke Morris TamneyI would open a high-interest savings or money market account, specifically for real estate investing, and save it there.

Hi Sara, An approach that has worked for me has been to post the job on Craigslist and be very specific about the details of the job - pictures, dimensions, - as many details as you can provide and then ask that they provide their experience level, tools they have and will need, their bid for the job, and when they're available to start.  

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. 

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.  

Which specific property type would you recommend when you mentioned "turnkeys"?

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.