Given the demographic of unbanked and underbanked population, the demand for cash will not go away in foreseeable future.

Taking the time to create a baseline business plan forces you to think through the "why," "how," and "what" of your real estate endeavors.

Quote from @Benjamin Finney: I'm curious what real estate investors and private money lenders like myself use to inform their businesses strategy and predict future market conditions.

I want to be somewhere I will enjoy but also somewhere that’ll be a good investment for either short term rentals or long term rentals in the future. 

As a land lord you need to be putting away $1 per day to pay for your future roof. 

What factors should I prioritize when choosing the best approach for my future success in real estate? 

At this point, I'm not willing to sink the funds for a paid CRM service but may be open to it in the future.

What are some pro & cons you noticed throughout your endeavor?

Leveraging the equity from your house hack for future investments, whether in STRs or larger multi-family properties, is a strategic plan, but ensure your initial property performs well before taking on bigger projects like flipping.

But, more importantly for future investing (and sanity) stay away from "guru's" and self proclaimed mentor's who have something to sell you.