I sincerely hope I'm wrong.

Don’t get me wrong SF is a great place to live but tough for landlords.

This property was my first, I feel like everything went wrong there: 4 flooding, bad tenants, overbudget renos but somehow still came out ahead in an economic recession (given enough time, real estate is very forgiving) so this property taught me a lot about what NOT to do.

As long as you have a good team in place it is hard to go wrong @Jesse Dadon

You should find out what is wrong with that A/C and talk to an HVAC guy you truth about the longevity of the unit or your portion of the unit.

Yes, there are commissions involved and make sure you don't pay anything like an application fee up front, but it's not wrong to pay people for their service (one of their services is getting your loan to the finish line). 

My plan had us both on Title, just tenants-in-kind(may be using wrong term here) so we aren't partners needing to file taxes together.

The last thing I want to do is start off on the wrong foot with the neighbors, especially if I plan to rent it out.

@Stephen Karagosian nothin wrong with that and you're right it can get a bit gimmicky at times.

There is nothing wrong with going this route.