There are a few odds and ends that will need to be done on this property.

So I would start in a construction trade doing odd jobs, raising cash for a project.

I know every property has its own pros and cons, but what are the odds that something goes wrong or not according to the plan?

If he indeed is getting paid at odd times, then I can structure it so that he can pay when he gets paid.

Would love to hear what ya'll are seeing out there or if I'm the odd person out not finding deals.

You will not be a good landlord and you and your husband will be at odds with each other as to how tenants need to be managed. 

I know that sounds a bit odd for a Ph.D. candidate to say.

I don't know about tenant/landlord laws in Connecticut, but you may want to take that into account too.The odds of your tenant fighting a small charge for the carpet--slim, but every dealing you have with a tenant builds a public image of you (not to mention speaks to your character).If the carpet is only a year old, then I, personally, would charge them replacement cost... any older than that, and it would be a depreciated replacement cost.The fact that you were going to replace the carpet (though it may speak to the carpets age) wouldn't directly have any influence in my decision to dock the security deposit.

It was odd because I did my due diligence and checked out much of their old work.

If the building has gas heat then obviously they're not using oil for heating, but you can see if you see any odd, old looking pipes (not water, not gas, pretty narrow and often bent at less than 90 degree angles) going underground.