(He stated the county assessed it for ~$1M, but I found the closest matching parcel to what he described at less than $870k.)

By going through the process end-to-end this way, you will learn how to find/finance/buy investment RE, how to repair/remodel, how to manage, etc. with those lessons in hand you can assess and mitigate the other risks mentioned.

I have many more concerns about this topic, but I don't want to hijack what others have to share.BTW, I have over 10 years of storm damage assessment experience with the highlight having been hired by the Department of Interior that oversees the National Historic Registry of Homes. 

What is the most efficient way to obtain accurate insurance quotes to assess cash flow.  

The financial health of the association and their ability to hit you with fee increases and special assessments are mostly out of your control.

I see multiple foreclosures needing rehab priced at their assessed values. 

The house needs a lot of work, but I think (I'm pretty sure) that I can buy the property ($35k) and do the renovations ($30k) for around what the current assessment is at right now.  

I had one that looks the same, once we opened it, there was a water leak that has been there for years, no foundation settlement, I assessed it to be a sink hole type and lateral movement of soil.

So if I purchase a Property for $60,000 ( a foreclosed and or distressed property ),and I assess the Rehab work to cost $15,000 ( includes labor and materials )The ARV in my area on a house like this would likely come in at $110,000So ARV of $110,000 x 75% LTV = $82,000$82,000 - $75,000 ( are All In costs on the property ... purchase price + the money for the rehab work )  =  $ 7,000If I wanted to do a Cash-Out refi. as Soon as the Rehab work was completed .....

Using the calculator here on BP I estimate 13 to 15 % ROI as a rental.Market value and tax assessed value are very near my offer point but with some TLC I think I can refi to a fixed loan in a few months to pay off a hard money loan.