Protection from lawsuits is a big item to consider as well, especially in higher price range properties. 

It’s ran like a business, not a personal investment.Given the heavy workload I have being the CEO/founder of the wealth management company, my wife has set up a well oiled machine on the property management side, due to her perfectionist drive however, it still means that she's constantly dealing with tenants and toilets and replying to items at all hours of the day and night.

The owner also needs to save for big ticket items that may need to be replaced every 10 or 20 years such as AC, hot water heater, furnace, roof.  

I have used both Traditional (pre-tax) funds, Roth and HSA.

Your renters will destroy these items and want you to replace them. 

Will itemize for brevity purposes:- Mother wants to move to Saint George, Utah and get a home in a 55+ community- Me (son) has cash and wants to buy the home for her.

.- The 203(k) will allow you to bid on properties that need repairs that won't qualify for a traditional mortgage => less competition => better purchase price.You will need to find a great local contractor you can trust to supply the required bids to qualify for the 203(k).- After closing, you can do some of the work yourself to save money, but the program doesn't allow you to pay yourself.You will want to buy a Class B property, maybe Class C+, in an area that seems to be improving.

I agree that DealCheck (or the BP calculator) does not provide enough tools or functionality to analyze those types of transactions (yet).But I would argue that it does a great job at analyzing more traditional buy & hold SFRs and multi-families, as well as flips and rehab projects. 

So I'm guessing it might depend on your state laws and personal situation. and make sure you know of any sticky items that would eliminate the protection you get from the LLC.

This is just one item.