She has proven to be unreliable and I suspect that she is gaming the system.

All modern furnaces have more repairs because of the complexity involved in safety and efficiency.I have proactively replaced 40 year old HVAC systems, because it always seems they go out in the cold of winter or heat of summer - at the worst time! 

If your lender has all the documents they need from the buyer and there are enough comps in the area, they can type the information into their system and see if it qualifies for a waiver.

My tip, work on systems, tools and marketing before you quit your W2, so you have your lead gen automated and can focus on working with people and not have to take time to build systems.

Do you use a software/system with your property manager to keep track of all rent collected, capital spent on repairs, and more to stay organized?

I have never done the rent out rooms but seems like a good idea if you get some systems in place.

And in reality, in 35 years, you will have 1-2 more roofs, a few HVAC systems, a new kitchen and baths or two, repainting many times over, etc.

@Matthew EganEven if short term rentals are not explicitly prohibited in the HOA bylaws, I would be very careful about purchasing in an HOA unless there are already a lot of short term rentals in the neighborhood as all it takes is a vote to change the bylaws and prohibit HOA's in the community.     

Quick questions getting started - 1) Which app or system do you use to manage the details of your properties?

So I hired an attorney because this is my first eviction and the timing was all wrong, the attorney left the US for 2 weeks and the court hearing was yesterday, took 4 hours because the city systems were all malfunctioning and Magistrate wasn't able to see our paperwork.