Context

I'm about to close on my second deal, and am in the process of exiting my first. A lot of people in this group already know what my mid-term strategy is, which is primarily cash flow focused and relies on acquiring a small portfolio of 2-4 unit multi-family properties.

I'd love to get some feedback from this group as to how everyone manages their various accounts.

Research Takeaways

Most of the research I've done on this topic basically results in the following takeaways:

• Separate your accounts. One popular option is to make an individual account for each property, but at the very least separate
  personal/RE-related transactions.
• Talk to a CPA
• Talk to an attorney

The advice is practical, of course, since every investor's situation is different and the structuring of accounts is highly contextual based on the individual's goals / investing strategy.

It's also infuriatingly general advice. I want stories and details, of both mistakes and successes, none of which seems to be readily available online. I want to know about the lender that turned you down because your bank statements were impossible to sift through. I want to know how buying a burger using your business checking debit card, or paying for an inspection with your personal card, got you into a hot mess come tax season.

Mini Story Time

My first deal was a flip, during which I was caught off guard multiple times when I was asked to pay for things right off the bat.

I didn't have time to set up my accounts properly, and I had no real idea what I was doing. As a result, I was using a Chase personal checking account for... basically everything. I had set up a business checking account with Wells Fargo, but when it came down to it, I couldn't afford to wait several business days to consolidate funds into that account -- I needed to send payments ASAP.

Not the most ideal situation. But how should I proceed?

Current Situation

To speed up transfers between my personal and business checking accounts, I created a business checking account with Chase. My ideas moving forward are as follows:

• Perform all real estate related transactions through my single Chase Business Checking account (what implications are there if I use a business checking account vs personal checking account?)
• Since it's easier to create a bunch of personal checking accounts, simply create a personal account for each property. This potentially gets complicated though. If I'm using borrowed money, where do the funds go if I use some of it to acquire Property A, and the rest to acquire Property B?

I'd love to get some feedback from the more seasoned investors here, specifically regarding my current situation. But also feel free to leave some general feedback for the good of the community.

Thanks!