How to Handle Charges on Personal Credit Cards

[Llewelyn A.]

I would like some opinions on something that probably happens every day in the life of a business person.

Let's say hypothetically, you own 100 Main Street, LLC.

You were denied a Credit Card so all you have is a Debit Card, but you don't yet have enough money to pay for some of your capital expenditures.

You do have $10k Credit on a Personal Credit Card that you have yet to use.

If you go ahead and pay for some of those Capital Expenditures, for instance, a new boiler for $1k, a replacement fridge, $1k, etc. is this something that would pass an Audit of 100 Main Street, LLC if you claimed the Capital Expenditures on it's books?

What about smaller items, such as printer paper, etc.

Each one of these items would come with it's receipt and saved for an Audit.

Will the fact that you made the claims for these expenses AND have the receipt have enough evidence that these were NOT personal expenses but rather business expenses on the LLC?

To expand this hypothetical scenario further, let's say you have a Personal Credit Card that gives you a LOT of perks, for instance, airline miles, hotel credits, cash back, etc.

You want to use this card for ALL your business purchases and get the benefits.

Will this fail an IRS Audit even though you have all the receipts and the Credit Card Statements?

Will the fact that you may be making personal purchases, such as buying a movie ticket, etc. matter as long as you only claim the business expenses?

What happens if you put 10 of your Investment Properties into separate LLCs. Are you expected to have 10 separate Credit Cards, one for each property? Or can you use just one Credit Card but allocate the Purchase Transactions appropriately?

What is the right way to do it so that:

1) The IRS would be fine with it

2) Not open the door to piercing the Corporate Veil

How have you done it in the past?

Thanks!