Therefore, while it's not the wife's homestead, she gets the benefit of it being her husband's homestead. 

If you are looking to use it you probably see it as a solution that produces specific benefits.  

Moreover, you have much higher overhead than most experienced investors.In a REIT you are missing out on all the tax benefits. 

I don't think this is a good idea for the sole fact that you intend on selling after his passing.Once they pass (which I hope is a long time from now), those who inherit the house will benefit from the step up tax basis, meaning the net proceeds could be TAX FREE.

We will inevitably work with a CPA in the future, but are there benefits to starting that relationship now?  

It may be a mute point depending on the tax benefits that you uncover.

Homes in need of repair or renovation can still be found at competitive prices, creating significant upside for those willing to invest the time and resources.Rental Market Backup: Investors also have the benefit of Indianapolis’ strong rental market as a fallback option.

I am grateful to any kind people here that can give me any insight on how I can make decisions that can benefit me financially. 

While I’m proud of the success of this project, I now realize that I could have benefited from starting my own investments earlier.

Historically speaking, STRs will at least allow you to cash flow right out of the gate and when you add in the appreciation and principal paydown and tax benefits, the returns are 40% a year or better on most of these deals.