Welcome to BP community @Peter Grabas It is a great place to meet new friends and learn about various aspects of real estate and more.

D.C. is a anomaly and can be very difficult to deal with from the tenant aspect.

But then, it becomes vital you start to seriously separate yourself personally from the business as much as possible, because likely you're still considered the "property manager" and then tenants might consider suing the "property manager", so some people even separate their property management aspect of the business into a separate S-Corp and furthermore put individual properties in multiple LLCs. 

Glad to hear everything worked outI see you're in the Long Island area, if you'd like to join a meeting of our Real Estate Investor group we meet monthly, I list the events on Bigger Pockets in the Classifieds/Events & Happenings sectionOur next:  https://www.biggerpockets.com/...It's very informal, open discussion (but you're under no obligation to share anything if don't want to), all aspects of real estate 

Let them know how happy you are with other aspects they are managing for you etc.

I've priced this so that $5k in repair costs doesn't materially change my IRR, but two things at play 1) my desire to build in as much cushion as possible for my deal #1 because I'm nervous (side note I even negotiated my mortgage rate down 10 bps last week) and 2) I think certain aspects were misrepresented during the showings so I want seller to make whole, on principle. 

Welcome to BP community @Eric Magray  It is a great place to meet new friends and learn about various aspects of real estate and more.

Was she employed by someone else in the same business she is starting and learned every aspect of it and now wants to go out on her own?

I realize that there are many more important aspects of completing due dilligence(referrals, background check, etc.) but how much weight does the appearance of the actual estimate they hand you carry in choosing a contractor?

I'm not exactly sure that any of your examples define a "pushover."