Your costs are fixed and so you probably can't provide discount financing. 

@Matthew Crane the answer is - maybeAt best, you can claim some of these indirect costs as startup costs. 

Every item has a lifespan and collecting maintenance/replacement costs should start as soon as an item is put into service.There are lenders that will provide HELOC on rental properties but they are not extremely easy to find.  

My question is, if we buy the home using a conventional personal loan while we househack, what would the costs and process look like of transferring the house and the loan over to an LLC?

In my state that would be an expensive change as I would be paying state transfer tax on the move along with other costs plus I would need to consider whether I wanted to buy title insurance on the property for the new LLC.

We expect to have holding costs of $15k to get through the off season and the condo is pretty updated so we would only be spending $10k in renovations (updating the bathroom and then finishes in the remaining rooms).

I'm wondering if it's worth the crazy labor cost to pay someone to do the work, or if it's a project I could do myself.  

That's three months of mortgage and utilities, the cost of flooring, and the cost of painting.

That is not reflected in the lawsuits related to this issue.You make no mention of the escrow costs or tax implications or transfer taxes or scrutiny that is involved with a deed back.

Eg if owning a house for the mortgage, insurance and taxes alone would cost you over $3000 a month (mortgage alone on a 25 year amortization for $500K is $3000 a month, goes down to $2700 on a 30 yr mortgage).