I would avoid working with Leslie Pappas / Archer Investors at all costs.

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.

I would say it depends on the cost of the STR.

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.

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

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.

If there’s a significant difference, it might justify the cost of adding more beds.For example, we manage a 4BD property where one bedroom is currently locked off, so it only sleeps 6 (1 king, 2 queen).

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

At least his apathy only costed you $1500 and indigestion.