Any advise or thoughts on this process?

San Diego city is in the process of formalizing their STR legislation. 

Whether you should do so will depend on the amount of realty transfer tax you need to pay since it's not cheap to hire an attorney to handle that process for you.  

If there is no contract, no license, and no process, nobody really knows who said what and when.

It was an easy process and I was able to interview my CPA several times and check her references prior to going under contract with her. 

We are in the process of moving to a new home in Buda (Hays County, 20 mins from Dripping Springs) and while we wanted to be in Dripping we couldn't make sense of it.  

I can pay off one $50k credit card "A" easily 18 months later, then use that $50k available line from credit card "A" to pay off credit card "B", then use the $50k line from Credit Card "B" to pay off Credit Card "C", repeat the same process...If I stop buying more properties, I can use my monthly cash flow to pay off all 4 credit cards before the 0% interest rate expires.

My background in real estate/rehabs has been full gut job remodeling houses that my parents have lived in as well as remodeling my current home, at one point I was a mortgage loan originator (helps knowing how mortgages/financing works), and I'm currently in the process of getting my home inspection certification to help identify issues for my own benefit was well as generate additional income.  

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?

I'm also in the process of building a spec house with a partner in a Texas resort area, which is a first for the both of us.I think I am unique in that I have only ever used commercial loans to buy investment property, which I hold in LLCs.