I don't know where she found this one home, it was a prefab and $8,000.00 lol and damage was minimal to say the least.

You indicate you've nearly pulled the trigger on an investment...What investment opportunities have you been looking at and how did they fall short of what you hope to accomplish?

Well after signing and re-signing an 106 page contract, plus some backup paperwork, we're waiting for counter-signed docs and to open escrow.The system is super confusing as they have automated emails that go out indicating your paperwork is incomplete, even if that is not the case....but hopefully everything is sorted.It's an adventure for sure, but given the expected value (and more importantly expected rent) I'd be happy to jump through the hoops again and again.Now I suppose the question is when it might be reasonable to have a conversation with the tenant......this will be my first tenant-occupied purchase.

There are other reasons that might indicate now is right.

If rentals, it indicates that the landlord didn't care, and when landlords around you don't care you have an area that at some point will decline.

The fact that he does not have leases in place is an indicator that this property is very poorly managed.  

Welome to BiggerPockets @Marcus Nielson As @Brandon Turner indicated the forums are a great way to see what is going on in your market.  

We have minimal leverage, do our own repairs, and do not withdraw any money from profits at this time.

Great way to learn the ropes and get the experience while minimizing your risks/learning curve.

No one knows what enough will be, but if you have a good indication that there is a lot of activity, look to make the offer that gives you that good deal that will make you feel good either way.