Open to potentially purchasing in all 2-3 locations simultaneously, depending on options.

Is it feasible to finance both properties simultaneously, or should I wait until next year to sell and purchase my personal home?

You can't sell two primary residences simultaneously and take advantage of 121 exclusion.

My goal is to eventually get to a higher cash flow in the years to come and simultaneously build equity in the property.  

Instead, put it in a wholelife policy, take a loan out against it, use that for the down payment, and have the policy gain interest while simultaneously acquiring a tangible asset and using rent to pay back the loan.

This assembly will also meet the current Philadelphia fire rating assembly requirement for new builds so you could simultaneously make the building safer as well. 

This phenomenon explains how people might be unaware of their lack of knowledge while simultaneously believing they are more knowledgeable than they actually are.I hate the phrasing "you don't know what you don't know".

As others have suggested, you can simultaneously raise capital on behalf of other GP' and seek an inside look into their operation and gain additional experience this way.

As you surmise, there is no way to avoid the deemed gain on transferring it out of the Federal corporate structure, into a pass through structure.There are potential ways to to transfer out the future appreciation while leaving the bulk of the 'old' appreciation in the S-Corp, but no way to get that 'old' appreciation out of the corp without triggering a gain.Last item to reiterate - this gain is at the S-level, so it’ll give rise to S/H basis (while simultaneously reducing basis via the distribution).

I could see it being easier because you focus on the investment side and the buying/selling side of things rather than having to do all that and simultaneously either fix the place up or manage the rehab.