The plan is that he will transfer the loan/deed from his current mortgage in 2021 and hop on the Oregon property loan/deed which will allow me to be released from it.I've been told removing my name from a loan is not easy. 

Make sure the seller has them all if he's going to hold them as collateral - chasing down titles can be an impossible task sometimes.Also make sure the titles transfer automatically if you pay off the park and that the balance on the park loan drops by the release price on the home when paid.

As far as transferring your properties into a LLC, its discussed just about daily here on BP (and I've posted on it a lot), but be very careful about doing it. 

There are plenty of transfer skills you will bring in as an agent even into a different market.I'm sure similar to NY, Philly can be street by street with some pretty hard boundaries.

With the buyers funds in escrow, you pay the seller, keep the fee and then transfer the title. 

Alternately some people close in their personal name for a conventional loan and transfer title to the LLC, but that has it's own set of risks.

I don't know actually, but I wonder the reason IF...Would a city push something like this in attempt to drive up ownership by raising the barrier of entry/operations for noon owner-occupieds?

In my case the solution was to place my name on the house deed using an interspousal deed transfer and then the underwriting issue was gone.

I also require each tenant to carry renter's insurance with a minimum of $300K liability coverage ($500K if they have a dog), naming my property management company and the property's ownership entity as additional insureds.

Is there any way I can setup both closings on the same day at the same title company without the original seller knowing i am transferring it the same day.