I do think you have gained something in this experience.

Are you looking for something livable and could cash flow or are you looking to gain a lot of equity through renovation.

I think I should also note, the main house is in my name only and would not be subject to capital gains tax.

Capital gain tax exclusion.What did you pay for the house?

@Lella Bennett Answer from a very trusted Title source that has nothing to sell you or gain by this:They are not covered anymore as the LLC is a completely different entity so it is not considered "Arm's Length".

You have two nice places there that will provide some good long-term gains as well as make money now.

@James CasellaGreat job on gaining knowledge.

Finding a fixer upper can be the easiest way to gain appreciation.

I am looking to inject (contribute) some money into one of my LLC to finance some new acquisition this year.I am refinancing my home (that is under my own name) and will use the cash out as contribution into the LLC.It is my understanding that while you can't deduct new mortgage or refi anymore on your personal home, you can still deduct all its costs when it is used for investment (by deducting from the investment income/gain).What would be the proper way to document this transaction in addition to the schedule recording the contribution in the LLC book?

Lower capital gains tax as compared to income tax What made you interested in investing in this type of deal?