By doing so, you’ll set the stage for clear boundaries, allowing you to be both a friend and a landlord.Rent Payment Made Easy: Online Rental Property SoftwareCollecting rent from friends can sometimes lead to awkward conversations and delays.

How awkward is this going to be?  

It was an awkward and uncomfortable situation for all and escalated for the entire year. 

It sounds awkward.

For now, the neighbor’s testimony should be enough, assuming they’re willing to testify anonymously to get rid of an annoying neighbor.Now, even if I have the evidence and neighbors testimony and decide to sue, the courts don’t grant evictions for breaching the contract then that could be a waste of money and time and it’s an awkward position to be in.

@Cesar Ruiz Riverside city is very much pockets of different types of houses it is not like some cities where you can generalize "east side good, west side bad"  In general though I prefer newer builds to the older ones or the more awkward 3bed 1 bath style.

@Miguel Urquiza and @Jennifer Gill I live in Spring, Texas which is 6-mins to The Woodlands.Woodlands is an expensive neighborhood and is hard to find a cash-flow rentals except you intend to use the property for STR (AirBnB). 

If this a friends/family partnership, this is a lot less likely to make the next Thanksgiving/ tailgate awkward.3.

I want to cover my assets, but also prevent any awkwardness that might arise from being both a roommate and landlord at the same time.Follow up question, what would a good exit strategy be for when I move out it 1-2 years when I try to rinse and repeat the process.All insight greatly appreciated!

(insert awkward smiling emoji) Unfortunately I couldn’t help them with that.