Whether it makes to sell the rental or keep it depends on your answers to these questions. the property is producing around $855 after property management fee, I have the same tenant for almost 3 years That's a little over $10k/year in cash flow, which is very strong yield for the price.

Since the original loan was apparently for a primary residence an LLC could never qualify because it isn't a person who would owner occupy the property. 2.

That Chicago near Southwest side is a great little area. 

Preforeclosure owner finance wrap, paid off the default payments and taxes with cash and assumed the owners loan.

You've left it to us to assume that you are charging under market rent which doesn't cover your costs. 1) Once you've figured out what you could be charging the public, knock a little off for a friends/family discount and present them with legal leases.

But I do have some family in Canada that have told me there has been some tax increases to the STR owners to try combat housing issues.

Heck I bought a “four plex” where there was an “owner’s storage area” exactly the same size as the other 4 units. :-). .  

The broker/owner, team lead, or seasoned agent could help another agent that is new in the business just like I did when I got into the business, I got a mentor to help me through gaining market share and how to do it.

$3500 in repairs with little downtime in getting it fully occupied.

You can list it for what ever you want as the owner.