The only way for you to understand the situation and evaluate your options is to ask a lot of questions.  

I understand this is a snails pace, however I am still a W2 enployee so all this will be a 2nd job for me.

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

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

I don’t understand how this isn’t a clear-cut case.

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

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.

I think a lot of investors are just scared of them because they don't understand them.