We currently have a contract assignment with the title company, and it's set to close soon. expecting the ROI soon, keep it up!

My lease agreement informs them that I expect them to do this and I have instructions this, and they have asked me for these very instructions, which I have yet to create.  

. - that were new when the S8 tenant moved in 1-2 years ago.Another challenge of finding S8 tenants is many EXPECT you to waive application fees and security deposits. 

You expect to start this or next year and in two  years have it making $500k net for you?

I would have expected most of the growing pains to be sorted by now. 

Just to take a step back...You mentioned your monthly mortgage on your current primary is $2900/month, but you expect rents to only be $2500/month.

.: Quote from @Scott Mac: hing just results in them turning into a ghost...Sorry if my timeline was not as expected. 

Even if they force you to refinance, the security makes LESS money because the loan is paid off and you are no longer paying the interest they expected. 

I would expect start-up costs such as stocking linens/bedding, upgrading certain furnishing and amenities, and pass-through costs for listing on the OTAs (like VRBO, Airbnb). 

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.