He retired at age 60, mortgage free, and with commercial tenants, tenants handle utility and repairs.

You will sacrifice some cash flow, but it will be a lot easier to handle and still produces solid cash flow and you only need to deal with turnover every few months (hopefully). 

Ironically, most books don’t advise on how to handle the challenges because that likely doesn’t sell as many copies of the ‘feel good’ variety but good information and how people figured out the challenges is out there if you look hard enough.  

Has anyone found any creative ways to handle closing costs if 1) you do not have the money to cover it or 2) do not want to come out of pocket to handle these costs associated with the transaction?

I had some investment properties several years ago that also handled all of the property management myself. 

Cosmetic issues come next and it's up to you how you want to handle these items (i.e. paint, new cabinet hardware, etc). 

We need advice and strategy for merging and handling our personal finances (recently married), RE and S-Corp accounting/tax strategy, as well as year-end tax prep help.Looking for referrals to accountants who also invest in REI.  

Your money will be wired to the title company handling the transaction, and ONLY to the title company (after you verified their wire instructions).

I’m just unsure of now how to handle him not wanting to leave on the first of September.

Also, my contractors are crazy busy with more work than they can handle.