Another good thing about that is that you can do a cost segregation study based on the percentage of the house that is being rented to your house mates.

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.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

If transferring the property to an LLC, be mindful of the due-on-sale clause, and note that an LLC itself does not offer tax savings unless electing S-Corp status, which is rare for rentals.To maximize tax benefits, consider cost segregation, bonus depreciation, and short-term rental (STR) strategies, which could allow you to offset W-2 income if structured properly.

Just let them know upfront they’ll need to restock for longer stays.

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

I would tell people today that if you buy a primary residence expect to stay in that home for atleast five years, especially with a FHA loan which has lower down payment as the current forecasts for home appreciation or very low which with closing costs on the buy and sell, it will take several years to have equity in the property and enough to be able to sell, so that is something also to consider.

In any case, successful wholesaling REQUIRES the knowledge, experience, and ability to accurately estimate repair and rehab costs and time.  

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

Way better returns on the cost seg than you'd ever cash flow from an LTR.