Also, if anyone has any general advice for me at this point it would be more than welcome.I am normally one to try to do things on my own, so I thought this would be a great opportunity to break that habit. 

It has so much potential for additional costs...Sort of devil's advocate, what's the harm in letting them go for free? 

The flip side to that being it's not what I would say is necessary for a non-luxury transaction to be taken seriously- actually harmful in these cases at booking time it seems. 

Instead of wasting your money you might want to print out the harmful effect of not replacing the filter for residents and make sure the tenants always get a copy and warning,     Also you can take it a step further and you can-write it in the lease that "if the filters are not replaced regularly tenant understand that this will cause a $300 repair bill at the end of tenancy, where tech or HVAC cleaning co. needs to come out and clean the system."

They have the most vested interest in you buying a solid deal, because they have to manage it every day.Just be careful of turnkey operators as they have a bigger vested interest in selling than managing.You might want to read our series about “How to Screen a PMC Better than a Tenant”, since selecting the wrong PMC is usually more harmful than selecting a bad tenant: https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processes

Habits are hard to break.One thing I learned with my wife, is that I have to “sell” ideas to her.  

No matter how much of a livable space it may resemble, if the basement or garden level isn't legal habitable space, you are taking on significant risk renting it.

This is going to always be a work in progress, as I’m trying to overcome 28 years of living a life thinking I’m the most important person in my life. 2) Put routines and systems in place that keep us on track for our goals, and correct us when we start veering off. 3) For the first time in my life Scripture study and prayer is a habit.4) Spent more time with family in the last 10 months than I probably have in the last 10 years combined. 5) Grew our rental portfolio from 1 property to now 8 properties.

Cash for keys will be the least painful and typically faster, but I will be doing a gut rehab and still need to provide 90 day notice with a no cause eviction and only because it won't be habitable during the remodel. 

I'm not an accountant, and this isn't advice, but as I said, you're asking the right questions and there's no harm in trying a new accountant next year.Best of luck!