I purchased a SFH in 2022 that I'm in the process of turning into two units with the intent to rent out one of them while continuing to live in the other.

Quote from @Mary Pastoral: VRBO's response to me "Definition Offline booking happens during pre-booking communication: after a traveler finds a property listing on Vrbo, you intentionally tell the traveler (or the traveler intentionally asks) to book or pay through you directly instead of using Vrbo to avoid paying Vrbo compensation.

It's a misuse if the wholesaler isn't informing the seller upfront of their intention. 

Thank you Bill. ill add the other expenses and report back in a year! 

But, typically, when I think investments, I think financial, meaning I am putting money in with the intent of creating income and/or appreciation on the money.  

If she's currently on Medicare but is trying to qualify for Medicaid, in some states the home can be kept if there's an intention to return (thus the allowable "caretaker"), but it will be subject to asset recovery upon their death, making it hard for the family to keep the home. 

If the intent was always to flip the property, it shouldn't be taxed as long-term capital gain no matter when it's sold.

She will say, "I will just text them that Ill come check out their issue etc"  and I'm like "first of all, we do not text them, we send them a message on the portal, do NOT give them your personal cell #"   yet she continues tod o it, I was told last night that we will definitely be letting her go. 

It's all come together pretty quickly in the last year and a half so I'm still coming to terms with it myself.The house hack is a four bedroom 2 bath house that my wife and I purchased as our first home with the intention of having it produce at least some income.

Are you intentionally using all three just to pick up some of the services they each uniquely offer that don't overlap, and to be able to choose which ones are strong in a particular area?