It sound like you have your area under control. 

Are you looking to do fix/flip or BRRRR?

To record it as December, you would have to back date it and the bank reconcilation would be off.

We do not accept zelle because of how easily it can mess up an eviction in Chicago.

It means nothing.

It sounds like at the current moment a HELOC would be the way to go as it can help keep costs low by only paying interest on what I pull out rather than doing a refi and being locked in to a higher payment regardless whether or not I find a deal.

Here are some thoughts on your choices:401k Loan: This can be a good option since you're borrowing from yourself, but it comes with repayment risk, especially if you leave your job.

I’m buying to improve the property, listing, service, etc so i do it right away.

Do we 1st do tax on the LLC and whatever we split 50 & 50 then each claims on their taxes ?

I have only been doing this for 5 years but what I have learnt is that it takes money to make money.