How did you get over that and pull the trigger - or know that it's best to walk away?

We only use CAP Rates when we are comparing one opportunity against another before pulling the trigger. 

Stocks are pretty liquid, BUT selling them triggers tax consequences and the timing of when you want the money for real estate purposes might not coincide with the best time to sell the stock.

Here are some of the types of “wanna be” investors who never seem to be able to “pull the trigger:”The Organizer – This individual can’t seem to ever get fully organized - and until they do they can’t possibly make a purchase transaction.

To trigger this exception, you must meet three criteria:You must sell your entire interest in the underlying passive activityYou must trigger a tax event, meaning that you must sell your interest for value in a fully taxable transactionAnd you must sell your interest to an unrelated third party, no family or close affiliates.Source Link

Yep, hands on local like you are doing is the way to go IMO ... if you are willing and able, have the funds, and have the discipline to NOT pull the trigger on anything that isn't a great deal.

Putting appreciated assets into an S corp can trigger gain. 

Find one you are comfortable with and pull the trigger.

@Matt Taylor I'm curious if you pulled the trigger on this and how it turned out?

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.