I would look for a market with solid cash flow but that is likely to appreciate and has a history of appreciation (do your research but maybe the Pacific Northwest has cities that meet this criteria).If you do decide to invest in San Diego I would suggest looking into a owner occupied (house hacking) detached duplex to quad financed via a VA loan. 

What do you suggest and why do you say it's the worst financing?

Our realtor also suggested this should be termed a Transfer for Convenience, but the attorney is not agreeing.  

Any advice or suggestions are welcome.

Any advice or suggestions are welcome.

I was juat suggesting local econimists have been a good resource on helping me to decide how to position myself to take advantage of what could be coming in my local economy.

Thank you for the suggestion and support.

Suggest you look up schools using https://www.greatschools.org

,You seem conservative in your approach and your $40k/year goal is so achievable in 5 years without leveraging up the wazoo like others suggested.

I think sending mailers to a specific group of sellers will be the best way to find off market deals with my criteria, and I am trying to learn the process and would love suggestions on search criteria that have been helpful when creating sellers lists, and what list broker you found most helpful.Oak Park, ILJefferson Park, ChicagoWicker Park, ChicagoBucktown, ChicagoLogan Square, ChicagoHumbolt Park, Chicago (nicer east pockets by Wicker Park)Hazel Crest, ILHomework, ILFloosmoor, ILTinley Park, IL"Northwest Indiana".. not that familiar to be honestWhere in greater Chicago am I skipping?