In NY you need to take a RE Salesperson course which is 75 hours after that is complete you take the license exam how ever you need a broker to hold your license.You can do courses online normally 200-400 but you can search groupon more often than not you can get the course for 90-150.Good Luck

I would offer to pay for recording fees and let the seller pay for normal seller stuff.  

I am looking to start a web page with the normal "Webuyhouses" .com with adding my city name at the end, unfortunately most of these domains have already been taken.

You might benefit from ones who deal with real estate law on a regular basis vs. your normal affairs attorney, but your call.

When I am ready I will move on to another house and continue to use this property as a rental.Has anyone else ever done this to get their foot in the door? 

The capex expenses, new A/C, new roof in the timeframes you estimate, combined with normal operating expenses will eat up your profits for sure.However, there could be an appreciation play here.  

Is this consider off normal practice or a standard transaction with SDIRA? 

I don't really understand why she's freaking out, seems pretty normal.

I see the desire to live in SF but just across the bay you can get a SFR for the same rent as your crappy 800 sq foot apt.

Typically they will be by about once a week and normally have a service truck with most of the common parts.