My biggest challenge right now is lack of liquid assets.One thing I'm very interested in hearing about from others is:-what was your investment strategy for rentals?

You will at some point be forced to at the least snake it which can be challenging sometimes or at worst replace it.If it is a flip I wouldn't be as concerned and just replace from risers up or whatever currently needs to be done.

The second something bad happens in life or challenging and people want to check out or say look what happened to me that is when people give themselves permission to fail.Life is tough,very tough but we all need to keep moving forward.When I was 16 years old I lost my dad to a car wreck suddenly, my best friends dad to cancer, and my grandmother all in the same year.

The engineers' opinion initially should speak to the severity of the issue.I'd break down an engineering engagement into 2 parts:First would be an initial visit and rendering an opinion on the severity and possible approaches in design to remedy.2nd would be the actual design and cost opinion(s) to remedy.If you're pretty serious about the house, I think if you pay the $250-500 that I think you'd likely need to do the first, that would be a GREAT investment more than likely from what you're describing. 

When we were looking 2 years ago, buying was an option, but the market is too hot right now for us to afford.It's a challenge locating a promising place while not local to the property, and that's why I'm turning to a trusted resource - BiggerPockets!

(the owner says no realtor/wholesaler so I'm not sure if we still can engage with an agent)-HS

If you get a good deal and stay under budget you shouldnt have any problems cash flowing.Best of luck Elivs and congrats on the engagement!

The fixer-upper duplex that I bought has presented many more challenges in learning how to properly fix up and maintain a building but the property is on track to perform very well (around 14% cash on cash).

This is all fine and dandy on projects around my personal home but would make evaluating a flip more challenging. 

Probably your best bet for cash flow here as a few clients of mine own them and do ok, but its a challenge dealing with that type of tenant and might not be the best first investment property idea..