They will think that you indeed are just taking advantage of the system. 

@Tyler Daniels Also, take advantage of the listing websites in your area.

You don't want to push too hard, but you also don't want to give him too much lee-way because he may see it as a sign of weakness and try to take advantage of you.

Loans fall into specific categories, and must meet requirements associated with that category.  

Preforeclosures and lease options aren't a good fit, unless you're willing to bring the note current, which nullifies one of the advantages of a lease option, that being controlling properties with minimal cash out of pocket. 

So I would imagine yours would fall into the C2-C3 category, subject to the appraiser's opinion and what information they can gather in the surrounding area.

As a long-time LTR landlord, I'd rent them out long-term, but only for a year or 2 to take advantage of the tax free gain. it comes down to market timing ,  really. 

Advantages: you can scale, the building qualifies for the loan, numbers work better, the building is treated as a business and valued by the NOI instead of being valued by the comparable in the area.Disadvantages/Things you need to be aware of:  If you have never done a commercial deal before usually a little harder to get financing so I would talk with a loan broker instead of going to individual banks. 

Looking to take advantage of the new ADU ordinance in Chicago.   

The bottom line is that companies will lose their competitive advantage if they can’t hire and retain talent. 5.