They are great tenants.These "Interns or Fellows" have Ivy League Backgrounds, Top Public Universities, Masters Degrees from Local Public Universities in STEM Disciplines, did time in the Peace Corps, etc.  

In my experience replacing a roof does not really add value, although it might give prospective buyers some peace of mind.

I am getting a structural engineer to review before and after the repair for peace of mind for me and hopefully the future buyer as well.  

Peace of mind would be worth the 1000$ super pooper.

Seeing his name on a preapproval letter along with an offer gives listing agents peace of mind and helps those offers get accepted, his local reputation is that good.

Enhanced Learning and Skill Development: By pursuing multiple strategies, investors can develop a more comprehensive understanding of the real estate market and broaden their skillsets.

This proactive approach not only enhances the overall appeal and functionality of the property, but also contributes to its sustained value over time.Legal Compliance and Risk Mitigation:The world of real estate is a complex and dynamic landscape, rife with legal intricacies that can be overwhelming to navigate.

This proactive approach not only safeguards your investment but also enhances the overall experience for both you and your tenants, creating a mutually beneficial relationship that contributes to the stability and profitability of your property.Maintenance and Upkeep:Regular maintenance is essential for preserving the value of your investment and ensuring its longevity.

It's an investment in your investment, and it will pay huge dividends in peace of mind if you take the time to go shake their hands, see the area, and take a look at some of their work (if turnkey, what props have they rehabbed/sold/currently manage, if DIY, what houses has your contractor worked on, what props does the PM manage?).

@Oskar Czeladko, there are multiple steps you can take to enhance the competitiveness of your offer.