No such Leasing Approval granted with respect to a particular Lot shall be transferable to any other Lot owner or Lot.

The personal purchase and transfer to LLC is a tested method that works. 

Job transfers or illness forcing them to be a sudden seller. 

It may be easier to do a Reverse Exchange where the Relinquished Property is held by the EAT/QI - since the entity borrowing the money will never have a change of control nor will there be a transfer.

However, I do believe they can be deferred or you can talk to lenders like local credit unions to transfer that student debt loan into something that is more stable or lower interest.

The tickets are transferable to Bigger Pockets Members, which I am. 

I've informed my landlord that I'd like to transfer the lease and am willing to help, he verbally agreed and mentioned he would put up + handle the listing.

My thoughts are don't lock yourself in for 24 months when the market might change in a positive way that changes your mind when it comes time to finally transfer the property.Instead, just lease it for 6-12 months at a time, and then re-evaluate as each lease comes up what is the best option for you.

Can Caltrans transfer their right of way across his property?

As a new investors, I would not recommend you take those on as projects unless you already have a very strong set of transferable skills such as construction, project management, property management and/or rehab.