Your bookkeeping system can tag income and expenses with a property ID or use subaccounts to keep track of income and expenses by property.Since you are a sole proprietor, there is no issue with co-mingling funds and using the same checking account for both personal and rental activities, but, it is much simpler for record keeping to have a separate checking/savings account for the rentals.I have charged stuff on my personal credit card for my rental properties, because I get "rewards" for my charges.  

The DBA is the business name, but YOU are the sole proprietor and file under your Personal SSN.Look at the DBA filing - - there is no SSN or TIN as it is also known.If you want to file under something other than your SSN, the create an LLC or S-Corp - - seek legal assistance to do so and to understand the tax implications.

I'm certainly not a tax expert so hopefully someone like @Steven Hamilton II can add to this, but yes if you buy and sell real estate as a business I believe you can be considered a "dealer" to the IRS, and you would file the income on Schedule C (self-employed) if you're a sole proprietor.  

Sole proprietor? "S

There are even Airbnb proprietors who rent out improved and permitted shed conversions for as much as $100/night.  

I have a Sole proprietor LLC since 2009 where I was doing consulting and training.

Anyone who make more than $400 net profit at the end of the year is taxed on it even though this might be their only income.With this in mind, can Michael N say "I am a business owner" (as a sole proprietor) prior to starting his trip to Kansas and start deducting all his business-related expenses from this moment on?

From a legal perspective, there are multiple benefits but primarily forming an LLC includes having multiple partners, versus just one sole proprietor, and you can shelter yourself from possible liability if anything were to happen on the property.

Every lawyer that’s commented on other posts with this question have stated LLCs aren’t worth the paper they’re written on when it’s a sole proprietor.

@James YangMakes sense.If you're going to operate as a sole proprietor, you should get E&O.