Pick your fights on a first come first served basis.

I completely agree and have conveyed this to the seller and he didn’t tell me to kick rocks so there maybe some negotiation capability. 2.

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. 

If you are not capable of staying on top of it all, in a few years that can balloon to over 100k in losses.

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.

When shopping for chargeback insurance make sure you are buying insurance, which reimburses you if payments are reversed and not a service that helps you fight back.

Read through it and make sure it is an area that will truly appreciate with you rather than fight you the whole way.

While I don't know your personal capabilities or background, the objective should not be to merely purchase real estate, it should be to execute on an opportunity where you do right by your capital providers. 

I feel as though it's a scam because even after all of the training you are putting out more and more money to see properties you have to fight to get to an then nothing pans out.

Meanwhile after the talk the newbies, the always believers, the desperate, and the just plain stupid we’re fighting to get to the back of the room to spend their money and sign up.