"Deep Pockets" Landlord - you need to buy those 50% inflated groceries for your family with less net income. 

After securing the deal, the buyer made my wife and I go through three-feet deep of snow to "winterize" the house so there wouldn't be any plumbing issues.It was a 2 hour drive there, and a 2 hour drive back.So much time and effort put into it for only $4k...

Think of the various scenarios that could happen with someone hiding in a house deep within a residential neighborhood. 

In short - in comes down to having a deep understanding of the hurdles investors face and being willing to put in more work than just saying "well, I submitted the file and the AUS/underwriter said no.

While the wealth of knowledge and experience on BiggerPockets is wide and deep, I would not trust a decision like this to the internet, I would ask you CPA and if you do not have one find one who specializes in this sort of thing.

I would do a deep dive into the market and determine whether you think it will continue to appreciate. 

I've syndicated multifamily offerings myself, and I have deep seated opinions in underwriting and asset management.There's one thing I seems to be consistent across the industry that I vehemently disagree with, and that's the expense escalator(YOY increases) for insurance.I STILL see people underwriting for 3% YOY insurance increases.

I guess I need to do a deep dive and see where the value is, but I know there’s no leads coming in.  

We wouldn't have to dive too deep and could issue you a preliminary term sheet pretty quickly, so you know what you're possibly looking at. 

But, if the cost is fairly nominal, maybe under a couple grand, and you have no experience in real estate, including owning your own home and hiring contractors for that, then it is likely worth it.I would always start with a deep assessment of where you feel you don't have adequate knowledge.