If you really mean that all 4 of you are on title and mortgages for both properties, then you may want to look into methods to clean up title, if you desire to separate from each other. 

Typically, the higher pricepoint/most desirable househack markets will take the longest to cashflow.

Estimated home price based on comps is $250-260k and rentals go for $1,700-1,800.We both believe that small multifamily properties are the smartest way to start given our ages and desire to probably retire by the time I hit 70 - 10 years from now (if we want to).

However, converting these into desirable, owner-occupied homes could capture untapped market segments, particularly as economic conditions improve.Age Distribution and Market DemandDiverse Age Groups: The presence of young adults and an aging population suggests varied housing needs—from starter homes to downsizing options.

Additionally, higher property taxes can sometimes correlate with better city services and amenities, which can be attractive to tenants.Cash Flow: While property prices may be higher in Philadelphia, rental demand is generally strong, especially in desirable neighborhoods.

Aside from the easier qualifications you can also get higher LTV on a 4plex for "cash out" and vest title in a LLC if desired. 

I am also on the fence considering that NPR is not that desirable a community. 100K purchase price with a $900 odd rent amount would go a long way in better, more stable cities.

The area here is pretty desirable and typically houses have appreciated around 5%.

Its like anything real estate related maybe 10% will succeed with anyone's training but that's OK the other 90 has the right to pay for the training if they so desire even though it wont bring any tangable results. 

Threats are made in hopes to bully other people to get what they desire.