Understand Their Process – Clarify loan requirements, turnaround time, and potential challenges before moving forward.

Another option is moving out of your place and doing a house hack.

When a lease ends they’ll suggest new rents and if the tenant hold be offered a renewal. some will offer to transfer utilities for you when it goes vacant, all should handle the transfer when a tenant moves in  With 10 properties I don’t “talk” to my PM more than 2-3 times a year.

Quote from @Austin Brummett: I wouldn't do anything right now except continue to save and learn, because you are likely moving soon.Lenders usually want to see two years of employment history, so you won't qualify for a loan any time soon.

Definitely will be moving my other rentals over to him.  

There is a spot on the brick exterior wall that you can move with your foot.

Funny enough, I was going to suggest you move out of SF due to the high cost ;-) I'd suggest going down the SF condo route to start as financing for commercial units is a lot more difficult than residential properties.

In the event that he moves out in a few years, I would turn the unit into a rental.Questions:1) Since I will be renting to a family member, do I still need to create an LLC?   

If you move title to the property into a trust for the seller's "Estate Planning purposes", you still need the mortgage company's approval. 

If I do choose to move forward with Rentvine, I will report back here.