:this is rather simplehttps://en.wikipedia.org/wiki/Cure_or_quit Matt, if they choose to evacuate, will they be responsible for rent till I find a tenant? 

 I would stick to bigger reputable companies and friends and family starting out.

@Travis Rotheiser Yep, it's really choosing when you want to "get some skin in the game" and which strategy you're going to choose to get to your goal.

The only reason to do that would be if you feel that the IRA would grow more effectively in real estate investments you choose than in the current investments.Because your husband is of retirement age, he can choose to take distributions from the IRA. 

My goal is to find lasting relationships while building a positive reputation in the area as I launch my RE investing career.If you are a knowledgeable investor in the area and need someone to research, help with maintenance projects, prospect etc.

Sure Chicago has a reputation and each neighborhood has a reputation but that is still not detailed enough to make a decision about whether a property is desirable or not..

Memphis Invest has an excellent reputation. 

Join REI groups (use meetup.com), maybe even try working with some reputable wholesalers to see how they do things. 

So, maybe I'm over thinking it but which one would you guys choose?

I also have taken early retirement and my husband chooses to continue to work for 5-9 more years so we will be moving into his home, and want to keep my house for a rental property.