Financial freedom can definitely be achieved in higher priced markets especially with the guidance of a good agent.

What goals are you hoping to achieve? 

I feel so lost on how I should go about to achieve my first rental problem. 

I would recommend you to read the following books -The House Hacking Strategy: How to Use Your Home to Achieve Financial Freedom by Craig Curelop and Set For Life  by Scott Trench.

I've fallen off in certain aspects of aspects of growth that I hoped to achieve through getting out in the streets and meeting people , providing value, etc. and when that got shut down I kinda shut down that aspect but as they say how we respond to tough situations in our lives says more about ourselves than the situation in front of us!

The paths I could see as useful at this point would be (but not limited to):- Sell your current home and purchase a home that performs excellently as an investment, and then add value to that one (getting your rehab muscle working AND simplifying the funding.- Keep your current home and pull capital out of it through a HELOC. 

This is a smaller effort, and more reasonably achieved for this scale.   

If I can keep that going long enough I may well be able to achieve the stepped-up basis at death and not have to pay some of those taxes due.

The reality is that we are now in a recession, and while 9.8% return might not be a realistic expectation in many markets these days, many markets are still capable of achieving solid returns.Another factor to also pay close attention to is cap rates.

So can benefit from that and shop around for prices to achieve your goal.