Supposedly on AirDNA it says I could make this is revenue but I highly doubt it!

Lots of pest proofing on the exterior.The biggest project was all the ceiling and wall repair required - had to demo one ceiling where the joists were split - only 2x4s plus water damage caused a major sag.

.- Bought an investment property for $110k on a second home mortgage 10% down (mortgage and deed still in my personal name) 2.75% interest- Renovated property this Spring (with all expenses run through an LLC with two friends, we each have 33% ownership)- Property is cash flowing nicely on short term rentals (all revenue run through LLC)- Current Zestimate $200kI have not yet deeded the property into the LLC, as I know we want to potentially refinance next year to extract our equity and use it to purchase another one.

With estimated monthly revenues of $3600/month once the project is done.

In your opinion, when considering the wholesaling business as a whole (from marketing tactics to purchase agreement assigning) what's the biggest problem that no one is talking about, that if solved, would make an impact for the better?

You and your advisors can determine how to allocate the sale price between the real estate and the business (non-real-estate) so as to get the biggest tax savings. 

Would there be any possibility of a lender including any revenue from the STR in my projected income?

If it's $2k/mo, we'd split the gross revenue after mortgage of $1150/mo - $575 to us for main/repair/etc...$575 to him to pay down the debt ($338k - Outstanding Mortgage $96k = $242k our debt to him - $575/mo)I'm wondering are there any other ideas on how we can minimize our payments or our future capital gains taxes that we'd pay when purchasing a property from a family member? 

@Sohrab Ansari;  @Scott KroneScott's points are really valid.One deal I looked at, they did not show property taxes, normally one of the biggest expenses. 

Then if they are not self managing shave about 30% off of their gross revenue.