My husband and I have had to constantly second guess ourselves on “are we being too needy or difficult?

Jason these problem can be visualized like these:a) Cheap Money regimeb) Expensive money regime (post 22) Then we do have always options for investment :a) liquid cash investmentsb) stock / bond portfolioc) Equity residential investmentd)Debt investment There's recent survey from Citigroup that showing a family office has different strategy when financial condition is moving from cheap money to expensive money regime, for example, during 2010-2022 cheap money regime, it's not difficult to be agressive in equity investment (such as buying rental) as spread is huge (6-8%) ; but during expensive money era, like someone also mentioned above, the spread is only 2-3% now.I can always generate 8-9% "almost safely" with public interval fund or BDC while equity is also offerig something like 8-9% IRR, so between debt investment and equity investment , is not big of spread.

The building department can be difficult fyi. 

Originally I thought Philadelphia should have some up and coming areas with deals under 110k, but anything even SHELLS of homes are over 150k in many areas, even some not so great/difficult to rent ones (not that I am looking for shells).

The UW is so inconsistent nearly across the board, it makes it difficult to truly offer a streamlined experience with clients, even when using the same lenders time and time again. 

Or what about the syndicator who did purchase the multi-family building in your narrow investment thesis  and did bet wrong on rates but a major employer just announced significant relocation to the municipality where the apartment building is located or a restrictive zoning overlay was just enacted making it difficult to add new density or maybe its the new commercial development just anounced that is anchored by a wholefoods and exciting nightlife exeriences a block away. 

There is certainly a case such as certain STR activities which may qualify for being able to be considered active income, but it's somewhat difficult to achieve this or material participation status where I think you're currently at.

I agree, it is a nightmare for me, difficult to make it work.

These days with high rates, I can see it being very difficult to find a property that would work.I second what Stevo said, huge difference between 4plex (residential financing) and 6plex (commercial financing).

If you find yourself second guessing your own preparation or dealing with more difficult topics such as a cost segregation, then it is probably a great time to at least consult with a professional.