My investor ended up bringing very little money to the closing table.

You bring something to the table, even as a new investor, and you take stuff from the table.

She has some cash offers on the table, but isn't really in a rush to sell and wants to try and get as much as she can.

Hey @Scott Gordon yeah, move on and scope out a better agent...spend some time interviewing and think about what value you can bring to the table.

I have a potential wholesale deal on the table.

If OP elects de minimis safe harbor ("DMSH"), he's going to have to capitalize as the expenditure is going to be more than $2,500.If OP forgoes the DMSH and instead applies the Betterment, Adaptation, and Restoration tests ("BAR tests") under the tangible property regs, we'd almost certainly have a betterment and/or restoration of the HVAC subsystem on our hands, so we'd also capitalize under this option.OP may be able to use the safe harbor for small taxpayers ("SHST") to expense the costs, however not enough information was given by OP.If SHST is off the table due to limitation, then must capitalize. 

I have my first wholesale deal on the table but it turns out that it’s with an agent.

😁Best of luck to you and hopefully we cross paths at a closing table one day. 

They are probably going to leave some of your money on the table.3) If a lender asks you for different documents 10 different times throughout the transaction it is time to find a new lender.

So basically under the table.