Aside from strategy you must understand how to underwrite a deal. 

Utilities are OFTEN overlooked so reach out to power, telecom, gas (or go all electric), water, and sewer to make sure you understand what it would take to get separately metered services from the primary house.

I don’t understand why everyone gives so much anxiety to the due on sale clause.

I would love to chat with someone who is a mortgage broker to understand your day to day workflows a little better.

I don't understand Ray.

I currently operate a few STRs so have a good understanding of that aspect although they're all located in touristy locations.

ouch....sure can understand why you didn't engage with them. 

I believe you mis-understand the process.

This would be my first real estate investment, making the decision even more critical.I understand that backing out would mean losing the $2,000 earnest deposit.

I understand the pros and cons of both so no real immediate preference.