I've found that what I value most in regards to real estate investing are the people who know about actual home repair and can approach a sale from that perspective.

But I’d take my scenario over yours any day because I’m not one car problem or home repair from needing to refi my mortgage.  

There is not enough money in the associations reserves (built up over time from members monthly association dues)  to pay for the repair of three roofs.

So I've been doing my own taxes in Turbotax for 20 years now (I only own 2 rental properties but both were BRRRs), and I finally got stuck on something and went to a CPA 2 years ago, and he reviewed my past 5 years of returns and pointed out that I had made multiple mistakes (incorrectly categorizing repairs vs capex, calculating basis and therefore depreciation wrong, failing to realize that certain expenses for a home converted to a rental property start being deductible the day the property was placed in service vs actually occupied, the list goes on). 

First, if you have a tax guy, he should answer these questions and not us.Second, it is unclear who is managing the repairs - you or your property manager.

If the owner is happily paying for repairs, the PM gets paid, the owner improves the value of their property, and the tenant now have improved living conditions.

That would give me enough time to repair the house to meet conventional standards and force equity for the cash out LTV %.

These records can give you a clearer picture of how well the building has been maintained and any potential expenses on the horizon.To address concerns about issues like a deteriorating foundation or sewer problems, ask the condo association for documentation related to past repairs and maintenance.

Most PMs are simply calling in a repair out of a rolodex.

Absolutely repair your personal credit first.