Buy a place and have roommates pay you money.  

Fast forward to now, 2 of the 3 tenants are wanting to end the lease at the end of the term and not renew, while the remaining 1 wants to stay and find 1 new roommate to share the house with (so there would be 2 roommates at this 1 house). 

I do have a roommate that is an electrician so there's that.

They could be rented out in the short term for roommate situations (yes techies are willing to share) but at time of selling, can appeal to a high income first time home buyer, thus have a high potential for appreciation.  

You think all situations are going to be couples only or adult roommates?

She had one eviction on her record from when she was 18- story went that she found a roommate on craigslist who moved out a few months into the lease and she couldn't pay on her own and didn't know what to do.  

You won't have to deal with roommates, except BF/GF, or large parties.Use only month to month agreements.  

Background: Two male, platonic roommates moved in on January 1.

Randy, this is exactly what I did with roommates, too.  

That said, there are always a smaller group of students looking for (new) accommodations in January (they discover they do not like residence or cannot get along with their current roommates).In our "family" units, we have noted that folks with kids move most frequently in the window from when school lets out in June and goes back-in in August/September.I also have an acquaintance who owns units in a rural community with seasonal employment and he's found that tenants are less inclined to want to move in the "off-season", but this is also the time when borderline tenants are more likely to do something unacceptable and/or become problematic.Ask a few seasoned landlords in your area and they should be able to tell you when more folks are looking and when they are battened down.