There is also a separate small cottage in the backyard that is rent ready as well and it's currently being used as an STR.

You might want to separate the market into "type selection" and "environment/neighborhood selection".

When buying an existing self storage facility, some operators separate out the value of the business and retail from the actual facility to lower their property taxes.

I know that everyone 18+ has to submit a separate application to rent a property.

Rather than just correcting the permit, we went ahead with the sprinkler system and decided to split the building into three separate condos.

Rather than just correcting the permit, we went ahead with the sprinkler system and decided to split the building into three separate condos.

I'm trying to understand some of the intricacies that separates the two.

@Daniel Hennek I am refi maxing four with a commercial lender under a separate entity ( not personal name).

I've been advised to set up separate LLCs for international investments and would like additional tips/advice from individuals who have done this already. 

What you choose determines if it is part of your personal return (Sole Proprietorship) or if you need to file a separate return anything else.If you choose a sole proprietorship the LLC can be treated as a disregarded entity.