Long story short I paid cash for a small SFR in early 2009 and had a guy move in right away. He was not a friend but someone I had known for several years. We just had handshake terms, he paid rent, took care of things and we agreed that there would be no rent increase for a long time if he didn't bug me all the time by fixing small things. Fast forward to last November, he had lost his long term job about the middle of last year but kept paying on time (he had only paid late once in the previous 5+ years and that was only by a week). The last few months he has been a week or so late. He has not paid this months rent and hasn't responded to my texts over the last few days. Is anyone familiar with Oklahoma laws, I am going to call him and try to visit with him this weekend to see if we can get something worked out. Knowing the guy, I don't THINK I will have to evict him, but I also am concerned that if he cant pay me, he cant come up with first, last and security deposits to move somewhere else.

No need to call him.  He knows he's late and you need your rent money.  As my attorney told a loan client of mine "no pay, no stay"

Send him a pay or quit today and let him know that it's business. 

Chances are he's already looking for somewhere to move and needs a little encouragement.

Good luck.

I went through this with a long term tenant several years ago.  If the money isn't there, it isn't there.

Start the eviction and hopefully he just moves out when he gets served the notice to quit.  If not, you should evict.  He is not going to magically come up with money with nothing coming in.

Originally posted by @Bily Elliott :

Knowing the guy, I don't THINK I will have to evict him, 

You may not have to evict, but you're probably going to have to do more than just hope he moves out because you remind him he's late on the rent.  You're going to have to get a little forceful in your delivery to him -- not angry or argumentative, just forceful.  State very clearly that if he can't pay by the end of the month that you expect he will move out by the end of the month.  You may have to say it two or three times in a few minutes time for it to sink in.

That approach usually works for me.  I've been managing property for many years and I've only had to go through the legal eviction process two times.  You run into the occasional hardhead every once in a while who wants to explain why he/she thinks they can hold on another month, but most people understand.  The problem is when people are broke and have no where else to live, they try to hold out for as long as they can.  It's your job as a landlord to let him know he can no longer hold out at your property.

Do you hold a security deposit from him?  If so, cash for keys might be a solution.   Tell him you'll give him his whole deposit back on the same day he moves out if the unit is left in clean undamaged condition, that you'll inspect it before releasing his funds.  Even if he does not have another apartment to go to, it's easier to find a friend or relative willing to let you stay with them if you can offer them some cash, so getting his security deposit back to him might cost you a few dollars in damages you find later, but since he's been such a long-term tenant, it's probably worth the risk.  

Find a landlord/tenant attorney and get educated on the process in OK.  If you're going to be a landlord, you need an attorney and you need to know the laws, so this is something you need to do even without this particular problem.

Then, follow the process.  Its the 20th of the month.  I'd be well on my way to completing an eviction at this point.  Rent is due on the 1st, late after the fourth, so on the morning of the fifth, I'd post a "pay or quit" notice on the door.  The 8th was on a Sunday, so on Monday the 9th, if I had not heard from the tenant I'd have filed for eviction.  I might not have gone to court yet (or, really my attorney may not have gone to court).  But if not, it would be coming right up.

The time for "working something out", in my book, is before the 4th.  I have done that more than once.  You're way past that point.  

Technically he is on a month to month agreement if there is no lease. Since he is not paying you should start the eviction process right away to get him going. If he moves out great, if not, at least you are getting the process started right away.

OK, I have done some reading, I will be getting him his 5-day notice to quit by tomorrow.  I guess I was just hoping that he would get things turned around and I would have another 5+ years of on time pay, or I guess I could hope to win the lottery too lol.  Thanks for all the advice. 

Posting a pay or quit in Oklahoma tends to open the discussion of moving out.  We are very willing to do a handshake move out agreement; you leave the place broom clean & I'll overlook the past due rent and not file on you in court. I usually take the opportunity to let them know that if they forceme to file, it will suddenly become very difficult to find another place to rent.