While this can be a viable option, it's important to carefully evaluate the potential implications and consult with a financial advisor to assess the impact on your retirement savings.Using your available credit on credit cards could be a temporary solution, but it's crucial to approach this method with caution.

The parties experience, strengths and availability are critical to ensuring  the partners duties and responsibilities are compatible and capabilities are sufficient to execute on the business.

Second, upcoming assessments towards building renovations can kill the cash flow within a second.

Wrong, well two of them are in a part of dc that is rapidly declining & no one in the family wants to take care of (and he certainly cannot) and has deferred maintenance on both, the other two are beachfront and a block from the beach, one already got it by a hurricane (no damage, but did trigger a special assessment & insurance skyrocketed) the other one just being near saltwater for 70 years takes a toll on a place, the other thing that happen’s with real estate over time is appreciation eventually rapidly outpaces rent growth so these aren’t as big cash flows as you’d think, a decision is was made to keep these properties both for appreciation and of course stepped up basis (most of these properties he bought for nothing and then depreciated the hell out of) while he has great assets and it will all be fine in the ends and we are all very lucky he has the assets to cover my grandmothers care, frankly trying to figure all this when he’s 88 and everyone is stressed just isn’t ideal, he probably should have just 1031’d up certain properties that had environmental and/or let’s just say locational risk into new or very new construction in the easy to rent burbs like a decade ago, while the tax implications always make selling at tough proposition, I think at a certain point in everyone’s life especially if there are lucky enough to have kept properties for decades should transition them into these easiest assets they can find in their market (you can even put in a reit or more specifically a Delaware statutory trust) to make thing’s easier for them and their family once they are no longer capable of managing those properties themselves. 

Then each propertyOwner along the road will get assessed on their property taxes.  

Sell.I am really concerned about trends I have seen in Florida where condos are being shut down due to unpayable costs/assessments, the building gets torn down and then a new one rebuilt and the condo owners simply lose everything.The idea of an HOA on sterroids makes me want to avoid them but then the added risk of shady tear downs makes me avoid condos like the plague.

It may be beneficial to consult with a contractor and real estate professional to assess the best option for your specific situation.

How do I even go into assessing something like this for rental value and long term appreciation to know if it's a good deal?

My favorite part is that we can take the percentage of the structures assessed value (assessed improvements value / assessed total value [including land] = Percentage) and the play our purchase price by the percentage to get our depreciable basis (not including acquisition/closing costs, of course).

In this instance, an appraiser may assess the Cap Rate of the Starbucks to be 5%, while the mom-and-pop shop is assessed to have a 10% Cap Rate.