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. 

In the past on a different property I've called the lender and confirmed it is okay to do this in order to not have a due on sale clause prior to quit claim deeding it into an LLC.I've heard sometimes the lender will say you must refinance into your LLC in order to quit claim deed it to not trigger the due on sale clause.

I’ve been researching for over a year and have knowledge, mentors, and potential funding sources but find pulling the trigger and starting on my own very difficult.

However if you plan on buying 3-4units, there is a trigger rule for FHA, it is called the self sufficiency test.

Quote from @Sarah Grace Haire: Hi Mostafa!

Would appreciate your thoughts on the above before I consider pulling the trigger on it.Thanks!

Would you pull the trigger?