seeking opinions on policy re roommate/boarder overnight guests

It’s not unreasonable, but it’s also not unreasonable if he decides to move out to a place that better suits his new lifestyle, under whatever terms he’s legally bound by. I assume he’s not on the lease with your landlord, did you get a deposit from him, or have him sign some other document that you can enforce? How great of a deal is the rent for the area? Are you sure you’ll see the same rental demand that you saw 6 months ago? How hard would it be if there’s a gap of a month or so between renters?

Of course you don’t have to answer my questions, these are just things that I would consider if I were in this situation. Personally I’d say that if you’re not going to bend the rules then tell the guy he’s welcome to find another place, otherwise they’ll be tension and it will probably be more annoying than having to see his girlfriend a few times a week. He did agree to these terms but “No overnight guests” isn’t something I’d expect someone to deal well with for more than a few months (unless the rent was an amazing deal), and I wouldn’t want a roommate/boarder (who I share my living space with) who didn’t want to be there anymore. That’s just me, YMMV.

Yeah, I don’t want that either. We do have a deposit from him and it’s a month-to-month arrangement. I think that I would see the same demand right now – I think this area is one of the few where housing prices have started to rebound (I know these are rentals, but still) and yet the job market is still very crappy. So I don’t really want to lose him even though I know we could find someone else, because as others have said, someone else could be WAY worse. He likes that we have no TV and doesn’t have one either…he likes kids and is sweet to ours…aside from his occasionally dogmatic statements and wild assertions about stuff he knows nothing about and his tactlessness (Example: the day after I learned that a dear friend was just diagnosed with bipolar disorder with delusions and was involuntarily committed after a frightening incident, roommate asks, “So, how’s the nutcase?”) he’s a good guy.

So anyway, yeah, we’re going to relax the rules but put some caveats and if he goes for it, fine, and if not, fine, we’ll find someone else. I appreciate the input.

Here’s a thought as well.

What if the rule was something to the effect of “not on a school night?” Because, I’ll be honest, my SO and I spend the weekends together. So the “not several consecutive nights in a row” thing would be a deterrent to me.

But if she could stay on Fridays and/or Saturdays then it wouldn’t be such a big deal for them if you preferred she didn’t stay during the week.

And that way you wouldn’t be counting the days in between, or wondering if you were going to run in to an unexpected guest on a Tuesday morning when the baby’s been cranky and you’ve run out of coffee.

Personally, my roommate knows I’m gone every weekend so she plans accordingly. My SO doesn’t have a roommate, so we don’t have that. But I have dated guys who have had roommates - and they just knew that I might be around on the weekends.

I think your approach “We’re willing to relax the rules a little bit, as long as you don’t abuse it, and here’s what we mean by not abusing it (let us know ahead of time as much as possible, not too many different guests, respect our space)” is good. Ya’ll are somewhere between landlord/tenant and roommates, and I think you’ve hit the right approach.
You could also add something along the lines of “of course, we expect you to spend as much time at her place as she does here”, which is the issue that usually comes up in rommate situations where overnight guests are acceptable in principle but cause friction.

That sounds like a good compromise. He is setting off some red flags for me (sneaking in someone who he knew broke the rules he agreed to is not a good thing), but you can give it a try and see how it goes.