I am hoping to learn more about how investors analyze their deals and make decisions, as well as looking to better understand general real estate investing.

My understanding is that the ballpark standard of "unless it would be outrageously tough" (something along those lines) is what applies if you're doing a rehab, seeking new permits, doing structural changes anyways, and things of that nature.For existing pre-ADA structures, my understanding is that the standard is more along the lines of "if it can be easily/cheaply done, you have to do it."

What questions should I ask to understand the property’s condition and the heir’s willingness to sell?

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

I understand business is slow right now relative to recent years, I'd recommend you get a better grip on being a REI agent.

That way, you have clear evidence if there’s ever a dispute.The the PM open to you talking to the cleaners so you can understand the scope of the job?

This will help you understand your options and decide if it's the right time to hire a pro. 

Start by deepening your understanding of CRE fundamentals, including net operating income (NOI), cap rates, and lease structures like triple net (NNN).

Start networking with local agents and investors for insights, and talk to a lender to get pre-approved to understand your budget.

That being said it’s worth understanding what’s working locally as your next step varies jurisdiction to jurisdiction.