I believe San Diego can be an outstanding cash flow market over a long hold.  

After making what seemed to be an endless amount of offers in this hot market, with a lucky turn of events of a sellers contact falling through due to the first place buyer unable to to afford financing.

Dividing it up into 17 acre lots would be an option as well.

Reach out to them and let them know you want to be an intern for a summer.

The designer should have a good sense of what to do with your place since they are an expert in this field so I don’t think it’s worthwhile to hunt around for styles you like. space planning and layout will be an important first step.

I have no experience there, but I am sure finding the right person to trust for a long time would be an issue here.

Buying when you plan to live in a property for only the next few years can be an EXCELLENT way to get competitive owner-occupant financing and low down payments on something that will be converted later into a rental.

The overwhelming majority of tax liens are ultimately redeemed, so buying in your name in search of anonymity down the road shouldn't be an issue. 

If they are a conditional approval, which is very rare, there will be an increased security deposit. 

I will gladly take any suggestions like meet ups, learning websites, books, podcasts, or even meet with other people who started real-estate investing to talk while I buy them coffee or dinner.