I know this is not a "get rich quick" sort of deal.

Even if it was in bad shape  or very bad shape after repairs , I think it would be much better investment than  a flip of some sort.  

that's a very good questionmy answer is many of the metric's folks use to decide what a good deal is and what is not, are very regionalized... whats a great metric in one market may not even be remotely possible in another.perfect example is the west coast buy and hold investor pulling their hair out trying to find a 2% deal.. and realizing they either don't exist or are so rare that you would be super lucky to find one.And those in other markets were the 2% rule props are on every block literally and they won't buy them unless they are at least that or much higher in some instances.So this puts investors in a paralysis mode not being able to buy ...

Provide more details on this flip transaction where you improved price so significantly.What sort of property?

I've had my fair share of restless nights and candid chats with my wife throughout these past few years but ultimately I always chose to take a risk so I could make some sort of progress.

For some people the fact that any sort of eviction filing would be on their record even if it never gets to the actual court date might be enough to get them to pay that lasts months rent. 

We are leaning toward some sort of private lending/creative financing but am unsure where to start.

My trip is essentially a vacation, but other than enjoying the unique touristy things each city has to offer, I really want to use the bulk of my time to explore markets and dip my toe in the water of investing, exploring different neighborhoods, looking at properties, talking to agents, investors, and whomever else can provide valuable insight on what I'd be venturing into when I'm eventually ready to buy.My intention with this post isn't really to turn this into a sort of journal with periodic updates, but mostly I was hoping that this post, and perhaps others in the future, could help me connect with some of you more experienced folks out there who may be willing to lend a helpful hand in anything at all real estate related. 

I'm imagining my home owners insurance would need to change somehow but I don't know of other things.For those that have done this sort of transition, do you have any lessons learned you could share with me?

He could change his mind, get judgments/liens against him and the property, all sorts of other possibilities.