There are pluses and minuses to that arrangement, just as there are pluses and minuses to conducting the entire business DIY by yourself, and many shades of grey in between ... but the fundamental truth in my mind is that RE is not a passive investment, it is always a business for somebody.

So my question is, is it possible to set up an arrangement where you find a short-term lease agreement on a vacation home rental, or some other type of home rental (possibly 1-3 months lease), make monthly rent payments on it for the duration of the lease, and after the lease is up, sell it to a "we buy houses" investor?

Well after many months contemplating about registering for class I am finally taking the plunge into the real estate field.

Gerold Koch if we arrange I️t again are you in ?

Financing to a buyer is accomplished in the TIC Agreement, and shares can be purchased over time, but sounds like you want a lump sum which is fine too.Your transfer of ant title interest will set off alarms with the due on sale clause of your commercial loan, the transfers should be accomplished with a "Subject-To" arrangement with each share and yes, the buyer can be responsible for the debt but only to you, not the lender. 

Most landlords will put tenants up in a hotel or some type of comparable arrangment.  

We have been contemplating the idea to add myself onto the house deeds and obtain a HELOC under my name because of my W2 income.Thanks in advance for your help BP community!

Arrangements can vary.

I do not know of any TK provider who provides washer and dryer although the other major appliances like stove/oven and refrigerator are typically market or neighborhood specific.A major reason this type of arrangement developed was maintenance.  

It will cost a little bit to do, but TRUST ME, it's so important on this kind of arrangement!