A good condo board should be saving money for larger projects as they are known in advance (eg every 25 years you need a new roof). 

Do you have a current need for that cash flow generated from the tax savings?

These small conveniences can save you time and money in the long run.For rent collection, you can try Rent.app, which is easy for tenants to use and keeps everything streamlined.

Inherently the steps are the same as if you were purchasing with financing save potentially less closing costs and ability to close sooner (if needed).The terms of your offer (ie -contingencies, closing cost splits etc) will determine what is different. 

Set clear goals, save for a down payment, and practice analyzing deals to build your confidence.

and if you don't have enough money to house hack in San Diego... save up until you do.and if you want to move somewhere else, house hack there. 

I'm looking for you advice with my overall strategy and garner any experience you might have to save me from learning the hard way. 

Could help you save some serious $$ if buying and selling there and can also get you access to their MLS systems.

My ultimate goal is not using my savings during this process, because I want to train myself from the onset to think creatively and not deplete my reserves instead of finding a better deal or more productive relationship.

@Laura GenoneI have my own information saved as a contact in my phone and it allows me to text, airdrop, or email my information to people I network with.