I am currently in my first year of my W2 job (post graduation), and after a year of listening to Bigger Pockets, getting my real estate license, and allocating funds, I have finally decided to dive head first into my first investment.

You won't understand something and need it beaten into your head ten times.

I own my own business/LLC and am open to changing that structure for tax purposes, such as putting it under an S- or C-Corp if it would help with this situation.)I appreciate any and all thoughts on this matter as I can't seem to get out of my own head on this!

Use him for your deal and he will have all your answers off the top of his head.

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. 

You're talking about some expensive conversions just to put more heads in beds. 

I work with a lot of investors in Vegas and they are all headed out to buy their REI.

The best time to prepare for a problem is before the problem rears its ugly head.

He was referring to a building boom that some builders were headed for disaster in their development.The same applies here. 

Basically, you want to try and get in the head of any potential buyers and what they may be willing to pay and why.