It's his business, his job site, etc. so it's up to him who to use on what part of the project.  

Are these sites legitimate?

A Business License is required to operate a short-term rental"That (from the SLC planning site) pretty much says it all.

Unused contingency funds, unless they were received directly from the borrower, must be used to reduce the outstanding balance of the renovation mortgage after all of the renovation work has been completed and the certification of completion has been obtained.The loan is not re-amortized.Draw Schedule:The HomeStyle program has a maximum 4 draw process.The initial draw can be up to 50% of the total project and can be for materials for the project.The final draw will be at least 10% of the total project as retainage and funds will be released upon receipt and approval of final inspection, Certificate of Completion from Appraiser, signed All Bills Paid Affidavits and Lien Waivers.Additional Draw Information:Ø Signed Draw Request by borrower and contractorØ Signed All Bills Paid AffidavitØ GMG review and approve the draw request and will release funds for disbursementØ A check will be issued in the name of the borrower and contractor and delivered to borrower via USPSØ An inspection of work to date will be performed at 50% completeFinal Draw Information:Ø Signed Draw RequestØ Final inspection/Completion Certificate will be required for release of final fundsØ A Title Update showing property free from lien or encumbranceØ General Contractor’s Lien Waiver AffidavitØ Affidavit of Completion GR will review and approve the draw request and will release a check in the name of the borrower and contractor.Change Orders and Cost Overruns:Changes to the initial plan are not permitted unless prior approval by Guaranteed Rate.

Site prep and permitting fees are not cheap.

I also think it's great that our property isn't sitting empty when we're gone and because we own and live on-site, our neighbors also keep an eye out for us. 

The variety of economic development grants/programs and the process streamlining that has taken place to date in Chicago is meant to encourage access for smaller and newer developers and encourage the types of "missing middle" developments that have historically been to small or the process to burdensome to move forward. 

You do know that there are hundreds of thousands of homes that are still valued at less than are owed for them, dating back to 2005-7, right?

Current lease term (expiration date, month-to-month)7.

We are fortunate that land development is something we've been doing for several decades, but each site presents its own challenges and rewards.