They might also want a fully-executed Operating Agreement showing who is allowed to open your bank account and sign checks on behalf of the entity.

@Jerome MorelosIt will be similar to what you sign with a bank, there will be a note (which is the iou which states how much you can borrow and at what terms and length)Then there will be a deed in trust (assuming California) which is a recorded document that uses the property as security.

@Tony Sherman, yes.Closing delays on buy side with title issuesMaterial delays, which can compound into contractor delays when you try to keep schedules tightContractor delays because prior jobs are not wrapping on timeContractor delays because you need to fire one and hire a new oneScope of work issues, i.e. no signs of moisture intrusion prior to buying, but all of a sudden you have a wet floor after a good hard rain.Closing issues on sale sideHow do you manage?  

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Should I try to have him fill out a W9 and sign some sort of contract since money over $600 is being exchanged for services? 

There is a contract signed by the previous owner for 5 years with 10 automatic extensions, so the contract expires in 2024. 

Example:-------------------Tenant A - Grandma Millie's Sewing ShopBeen in business 1 year, decently profitable, signs 5 year lease.Rent = $60,000/yearTenant B - Eye Doctor office.Been in business 5 years, quite profitable, signs 5 year lease.Rent = $55,000/yearTenant C - Subway5 year leaseRent = $50,000/year-------------------If I assign the following Cap Rates, I get these building values:Tenant A / 10% cap rate60k/.1 = $600,000Tenant B / 8.5% cap rate55k/.085= $647,000Tenant C / 7% cap rate50k/.07 = $714,000(or even $45k at 6% cap rate = $750k)-------------------I just made up all of these numbers.  

First gage their interest, if they are on the fence, you can offer something like $300 off first month rent if they sign a lease by this date.

I have called bandit signs to get on the buyer's list, leave voicemail, then get no callback EVER.

My challenge is that I am not authorized/signed up with the city to take on CHA checks, so that will take a while to get a tenant.