While you may have a 2Br that is not for the "typical" sized family, you will have many people also looking to downsize from their larger homes that they are holding on until the summer to list. 

I understand at this point there will be a loss I will have to incur, but I am looking for thoughts on if I should rent (knowing I’ll have around $5k a year to loose with renting and property taxes , but giving myself time/ hope of appreciation) or if I should just sell (locking in a larger loss on the property now).

And he has also made hundreds of millions in his courses, trainings, seminars, books, etc.He's also an intense, larger than life personality.

This can be hard to manage if you have a larger property with a regular size washer.

Or maybe there's less competition with larger cabins?

You CAN NOT target motivated sellers.The only way to get in touch with motivated sellers is for you to make it extremely easy for them to find you.Going after lists will be your doom.If you have $30K to spend on lists, sure, due to sheer volume you are bound to get a deal with some luck, sure.But if you come along with a humble budget, forget it.The reason larger budgets work better is because you can send a huge volumes.

., etc. that you have to do for a larger tract you want to subdivide. 

I now realize that this is only attainable in highly desirable locations and with larger or more unique properties.

There getting a fee, hourly, what's there dog in the fight?

Unfortunately we have a larger loan amount requirement.Good Luck