Also the property transfer tax is quite high, it can add up to around 13% and normally has to be paid in cash.

I've seen a few properties in Colorado mountain towns for sale recently with STR licenses that transfer with the property (rare to find because the waiting list to get a license is many, many applicants deep.

This greatly discourages any transfer of title until litigation is resolved and most title companies will not issue clear title during this time as the title is in play.  

I am trying to figure out if there is a way to buy an investment property with my VA and use my LLC for the purchase or a way to transfer it over to the LLC afterwards.

Certificates of registration are non-transferable and non-assignable.

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.

Hypothetically, if new tenants moves into property in August and transfer utilities in their name, would the true-up date change to August as well or would it continue to be May.

IT and Banking is transferable between nations and companies.  

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?

So there are no bank fees to buy the property and we are not limited in the number of properties we can do.The seller transfers ownership to us.