You can also assess a dollar amount that you value the cost of these requests to be, and ask for these as a discount from the purchase price or a concession to you for closing costs. 

Turbotax isn't going to educate you so unless you'd like to educate yourself and potentially make some costly pitfalls, then I'd outsource.

Streamlining Renovations for Efficiency & Cost ControlManaging multiple renovation projects at once demands an operational efficiency that can be tough to achieve.

Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.

This could make the sale more appealing by solving a logistical challenge for the landlord.Things to Keep in MindUnderwrite Conservatively: Make sure you account for all costs, including property taxes, maintenance, and potential repairs.

They have offices in many states and handle thousands of rentals.

Starting with house hacking is a smart move, especially in a higher-cost area.

To be brutally honest i don't care if it's at cost, below or above, I only care what it is exactly and how much. 

Here's the deal: One Hundred and eight seven THOUSAND!!!!!!!

There's other items such as this where it may be helpful to talk to a CPA/EA for a little tax planning, especially since you'll likely get caught up in the passive activity loss limitations if taking bonus on a single rental property as I often see.It's also useful to mention that even if you do the cost seg study (I'm assuming you're doing one to be talking about this), you'll still benefit from accelerated depreciation in the form of shorter useful lives on the assets where you received bonus from.