I believe the play is to either improve the existing building and raise rents or the zoning allows for apartment buildings and the lot is considerably big, so maybe build new.

If “wholesaler” (used in the sense of contract flipping, not people who close on purchase and resell) were required to disclose in writing to home sellers that they are not purchasing the home, are only trying to “flip” the contract, and the sale will only close IF a buyer at a higher price can be found, would this eliminate the need (if a need does exist) for government regulations being enacted and or for “wholesalers” to be licensed real estate agents?

Luckily you as a new investor have far more strategies and strengths than an existing investor with multiple properties. 

Any recommendations on an AirBnb Manager in Chicago to take over an existing asset?

Just realize that if you buy real estate with a heloc, be careful as now you are basically leveraging existing assets for new assets and many times people get over levered and in trouble in those scenarios.

Have the permit in hand, the building erected quote, banker says no downpayment needed since it is tied to an existing project that is very LTV favorable.   

In PA, there are no tax liens, only tax upset sales where you take title to the property subject to any existing liens. 

when we got word that a local off market carwash was for sale decided that it would compliment our already existent detail clientele and made every move possible to get it in our ownership!

@Joey Morgan if your client wants you to write subject to the existing mortgage, likely best to contact listing agent first and ask if seller is even interested, can save a lot of time if not.

Buying an existing place that needs upgrading might be more sensible but it will still cost a lot of dough.Plus the purchase of the catamaran.