That average person given limited access to a property is not going to have the experience required to know what to look for.Yes, i would have a couple of your most trustworthy contractors with you when you walk the property and i'd film the walkthrough / take as many photos as you can.With a full hour you can easily assess most of what would be needed to account for 

The tax assessment last year was based on the home's prior condition but fast forward to this year and the taxes have doubled.

I can give you dozens of examples of owners who believed they could care for their property better than a stranger.

Here in Texas, I’ve gone through hundreds of deals this year and maybe half a dozen deals were worth the investment. 

I do plan to verify these expenses and assess whether they include everything, like ongoing maintenance costs.

Have them do an assessment.  

Its easy to get complacent when the market has treated you well for a dozen years.

To assess the development potential of a 200-acre property without public utilities, start by consulting a civil engineer.

Consulting with a zoning attorney is advisable to assess the feasibility of your project and guide you through the necessary procedures.Hope this helps!

@Minnina SmithTo buy your first rental property, assess your financial situation, educate yourself on real estate investing, set goals, build a team, analyze deals, get pre-approved for loans, and start property hunting.