(Seller is also paying him 15k for closing costs) in the end, it’s doable.

I think any strategy is doable, but which is best (particularly for luxury markets like in the Bay Area)?

I don't think getting a loan with an LLC is all that difficult; your choices are somewhat fewer but it's doable if the LLC either has assets and credit history of its own, or you give a personal guarantee.And, since I haven't heard anyone specifically mention it, expect to pay several points and a higher interest rate if you are borrowing for the LLC--banks take higher risks by lending to a company versus a person living in home and those risks reflect in the higher rates.

I’m not saying there won’t be hurdles, but it’s doable.

.* it seems more doable to create a lease or sublease where the individual tenant gets access to a room and common dwellings.Feel free to message me to exchange more ideas. 

Take a look at careers within the RE industry that require some education but not a college degree: property manager (start your own company and get 50 properties under your belt - very doable if you are good at it); mortgage loan officer; real estate agent; real estate appraiser.

I also believe that 10 years is totally doable.

According to the post, it is do-able.

Would my proposal be doable (as more of a long term project) if I got my Realtors license?

The exact # is not important but I'm not too far off. next year is do able.