Being a wholeslaer is having a business.You are in the business of finding and buying land/contracts for a short duration and then immediately selling them.One typical expense for a wholesaler is all the advertising costs to find motivated sellers.

Hi! I am new to this arena, my husband and I are buying our first home with the idea to house hack. My long term goal is to buy within the next month, then within six months be ready to purchase our first BRRR or flip...

I assume a cpa would charge $300-$600 extra to sort/organize 5 properties receipts?

And people still have enough intelligence to sort that out, and to pay for quality knowing quality in selling/buying real estate = ROI.

You need to find a motivated seller that you can pitch to.

What kind of affect if any would this have on any sort of financing that is in the works to purchase the property?

After reviewing their apps, you can sort of tell who won’t ever be able to qualify or afford to buy a house.

Not to mention the paperwork pain involved with each claim Any thoughts on just not having any insurance at all, or just some sort of liability and really high deductible ?

@Wilson Vanhook  You'd have to finance that $100k in some sort of way if you don't have it. 

Example- finding motivated seller.