This is all made worse by the fact that there's no "collaborator" login (as other solutions have).

I look at baseline affordability and edge just barely up.

I ultimately decided to look out of state where the price points were more affordable and the numbers made sense + landlord laws are more friendly. 

I’m struggling to see how I can afford to get into a second house with my current DTI.

Get the biggest house you can afford and rent the other rooms out to military with BAH.1.  

I love how Mint was "semi-automatic", and did a decent job on its own although you needed to come in and tweak categories.All this to say, are there any other Mom & Pop investors out there with more complex personal finance that have found useful software solutions? 

But both should only invest what they can afford to lose.  

As home prices or interest rates increase, fewer people can afford to purchase homes, forcing them to rent.

I think a PA is the best solution.

Not the best solution because if you terminate your PMC, you may forget or delay getting your own insurance again.Interview several PMCs and ask a lot of questions about HOW they execute the services they provide.