Would that be allowed as long as we are not personally working on the house?

Completely lock/key separate and 0% owner personal use.

I purchased it under my own personal name on this first one, cause we were competing to get there quick and my EIN hadn't come in yet.We do our own taxes but I have no clue what to put for this house purchase. 

Section 121 allows a taxpayer to exclude $250,000 of gain($500,000 if married filing) joint on the sale of a personal residence that was lived in for 2 out of the last 5 years.

Obviously you can't have complete control on these but you can get a gauge when first speaking with the person.

I'd be delighted to make a personal introduction, and I'm just as eager to discuss life and real estate here in sunny Medellín, Colombia!

Here is a link to the Comptroller's guide to the non-resident withholding, which may have answers to your questions: https://www.marylandtaxes.gov/forms/current_forms/withholdin...If link doesn't work the document is called "MARYLAND'S WITHHOLDING REQUIREMENTS for Sales or Transfers of Real Property and Associated Personal Property by Nonresidents" which you should be able to Google.Good luck.

Other options I would consider is renting each individual rooms (this generally increase the monthly cash flow vs renting to a single person).

I like the area personally!

There is no need to factor in attitude or personality in the business.