I was thinking of buying an investment property with 20% down using a conventional loan then using the BRRR method to refinance and move on to my next project.

You definitely want to charge enough for deposits and such to help cover cleaning and light damage repair but at the same time if you charge too much people will just bring their pets in and never tell you about it.

My main one is having someone come clean my house. 

I'm listing an older gulf access home in SE Cape Coral and it's booked solid with seasonal renters and its pretty dated, clean but older (actually my age, 49 :).

@Rijm D. the lender you get the HELOC from will have their own appraisal method. 

The $50/pet I charged initially was a one time fee to pay for carpet cleaning after they vacate.

We will take care of all guest communication, listing details, cleanings, scheduling of repairs, confirming bookings, stocking supplies.

First, let me say thank you for posting your story and laying it all out on the table, The Good, The bad and The ugly.And I agree that there is no get rich quick method to real estate.

I would also question the $500 for getting the unit cleaned up unless it was just completely rehabbed. $500 doesn't go very far.

Once done, a competent CPA will quite often be able to file your S Corp and properly register it with the IRS.However, I've seen many occasions where I've had to go in afterwards and clean up the mess from improper filings.