Hi Joseph -  For your first scenario, if you acquire another SFH with a traditional investment loan, the rental income can count toward lowering your DTI, but typically only a portion of it (usually 75% of the rental income is factored in).

This is by far the most important factor in my opinion.

Also, what key factors are influencing your decisions?

Consider factors like retirement, landlord fatigue, property maintenance issues, or asset liquidation.

How much above market will be the determining factor whether I want to move forward or not.

If you didn’t factor in some amount for repairs and vacancy and CapEx when you vetted your property I hope you will do so with the next one.

Look for homes that scare most homebuyers & factor in your renovation budget when making offers.- Opportunities with additional income potential.

Just a note for you since I was just talking to a client about this: if you live in a high-income state or have privacy concerns and are living the digital nomad lifestyle, south Dakota has an interesting residency status program that can potentially save you guys 10s of thousands on income tax and have great anonymity. 

Now to the "DUH" factor; who's paying this ADDITIONAL $25k per FTHB money?

This will help you identify what market will have the most ideal factors for what you're trying to achieve with real estate.