You can meet local investors by registering to attend real estate events in your area: https://www.biggerpockets.com/forums/521-events-and-happenings6.

this is a prime example in the PNW when cities demand that U can only cut certain trees and you need to leave others..

Does anyone have any recommendations for a good contractor who can remove the tree roots underneath my driveway and repave the concrete?

@Maria Rina Boidon -  Your options can vary based on your current financial position and investment goals.

PS: I can help you get two or three out-of-state properties in Alabama that will cash flow, and I could also provide DSCR loans for real estate investors like yourself in Monmouth County. 

But how can we draw a line between repairs and replacement?

You can also search Google and read reviews.

Each loan product type has different rules and restrictions for using rental income to qualify for new purchase, and some can wreck your plans (such as the FHA 100-mile rule).

I've been pre-approved and assume I should provide that info, but what else would be helpful that I can send right away during the "interview" process to prove I am seriously looking? 

@Christine WilcherQualifying for another FHA loan can be challenging due to its focus on owner-occupants.