Hi @Jack Brown,The table below provides the requirements for second home properties. must be occupied by the borrower for some portion of the yearis restricted to one-unit dwellingsmust be suitable for year-round occupancythe borrower must have exclusive control over the propertymust not be rental property or a timeshare arrangementcannot be subject to any agreements that give a management firm control over the occupancy of the propertyIncidentally, it reads to me like a model match for places that you're going to have as a furnished rental or airbnb part of the year, and a spot for your family to vacation for part of the year too.

It's my understanding (and I am definitely not a tax professional) that you can only withdraw money from your Roth with no penalty if you meet certain restrictions.

You could possibly double close on it, but most short sales have deed restrictions these days preventing the resale of the property for at least 30 days and sometimes as much as 120 days. 

Here's a link to the raw guideline, if you want to attempt to decipher it.TLDR is that no you do not have to wait six months, but it has to have actually been a cash purchase, or other restrictions may apply. 

@Bao-Chau Tran you will need to check your HOA covenants, conditions and restrictions.

IL does have some restrictions; however, his ownership should be fine. 

Are there rent restrictions? 

Besides asking the builder (do you have any restrictions on percentage of investors buying property here).How do you data mine the community to find how many or what percentage of the community is owner occupied and which ones are not.    

Deposit, term length, interest, payments, and restrictions.  

Are there any rent restrictions in the neighborhood?