If the deal is worth it then why would e-signing a few pages be the hold up here?

Does it have to be an architect local to the state you are rehabbing/building in that would have to sign off on your plans or can any certified architect sign off on your drawings?

We did get negotiate money from them to help with roof repair, but now know they were not honest on their disclosure.Our inspector missed code violations, HVAC issues, pipes that had been worked on and issues hidden that had occurred while sellers lived in the house, signs of drainage and water damage inside the house that had been painted over, completely blocked dryer vent...and we are finding more daily.We have had the house looked at by a structural engineer and HVAC techs that has told us we need thousands (likely tens of thousands) of dollars worth of repairs to make this property able to rent and come up to code for rental. 

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? 

@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.

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.

@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?  

You got past the first big hurtle in real estate investment, signing up and reaching out in BiggerPockets.

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.