Central A/C is damaged beyond repair and needed to be replaced, which can't be done economically or with coopperation of the HOA and other neiighboring owners.

Your homeowner policy may cover minor repair work but probably not a large construction project. 

For example, what is the monthly revenue for the property and what are the "All In" expenses, including mortgage, taxes, insurance, utilities, repairs, etc...

You'll still have plenty of money to do a duplex/quadplex and give you breathing room (what would you do if you needed a large repair on the rental?).

Once you’ve got a little experience under your belt then you can attempt buildings that need more renovations/repairs or have had management issues.

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

Focus on distressed properties needing cosmetic upgrades where the after-repair value (ARV) justifies the rehab costs.Good luck!

It was also difficult to assess the heating situation after repairs since tenant refused to provide key to access unit for repairs and/emergencies, citing “privacy and safety” concerns.

I had miscalculated the repairs that would be needed to get the home back up to liveable condition and I had to go back to the seller to renegotiate the price.

A CPA can ensure proper filing of rental income on Schedule E and help identify tax-saving strategies, such as optimizing deductions for maintenance, repairs, and travel.