We had no issues with them thankfully. 

That would cover any screwups, but also incentivize the title company to remedy the situation without making a claim, since it appears to be their oversight that caused the issue in the first place.

@Joe Black an S Corp is not a great legal structure to hold real estate assets in, so the advice you were given was not wise.

If you'd rather not deal with tenant calls or maintenance issues, a manager might be worth the cost.You've put some great thought into your plan.

I have however run into issues like transfers being rejected by Baseline (from one of my own accounts in a traditional bank) when all the information is correct.

Your biggest risk if you execute the plan will be running out of money in retirement, either due to natural longevity and/or later health issues draining your resources.  

Both apartments are currently rented, would this be an issue in the future to get tenants?

We have bought in AZ, NV and TN and have had no issues since we have good property managers.

So you're essentially saying the roofer has no negative consequences for his bad, the city inspector doesn't have an negative consequences...and you have to pay someone to fix this issue?

Buy "Every Landlord's Legal Guide" by NOLO and start reading.