SF is a very unique market, and actually may be a great time to buy right now, especially if they can successfully turn the city around. 

Absolutely - East Hill is a really popular area for traveling heath care professionals, as well as military on short term TDY orders who are looking for furnished stays.Keys to success for my condo have been keeping the furniture fresh, and not looking like every other listing out there.

He became a contractor, worked hard, and grew a successful business that produced a lot of money.

Many successful investors started small, such as with house hacking or buying affordable properties to rent out.

Congrats on your success so far.Some random thoughts for you:- It might be difficult to tap the equity in the rental at this time given the current state of interest rates. 

I wish you all the success and please don’t hesitate to reach out if I can ever assist or support you in any way.

It's because they think there is some "secret formula" to success. 

I had an STR arbitrage before with some success.

I'd say they are both cash flow market. 

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.