Other than Property Management issues - what are things I should consider when investing in a place like Bloomington, IL?

If you are considering a property in a location you vacation to, you could also look at doing a second home loan.

I'd love to connect with you & learn more about what you are looking for in a deal!

In my experience, you are thinking through this correctly.I've heard lawyers say, if the loan is in your name (which it has to be for conventional) and the deed is in the LLC, you aren't treating the business as an independent entity and in a severe lawsuit, the corporate veil is pierced and the LLC can be thrown out.I agree that one of the best defenses is to run your properties well. 

You turn in your claim within a few days after moveout & they send you the money in a few days after approval. 

You're very close to the end of the year and you don't have all of your ducks in a row. 

Easiest and least costly is to go there and spend a week or so to get everything in order.Another one is to hire someone trustworthy and pay them to put it in their garage or in a storage unit for a month

However if you buy in a neighborhood where people do care or all  your tenants have cars, you may get shut down quickly. 

I redid the master bathroom by removing the tub and putting in a standing shower with white granite looking tile, and a custom glass shower door.

I have a good amount in savings, and as a first-time homebuyer, I believe I can lock in a low interest rate.