Learning on your first property will be a challenge, but having to deal with bad tenants will make it even harder. 

Maybe the sub $150k condos don't look as nice and don't have an ocean view but to see such a HUGE range in prices tells me there is something else unique to these cheaper priced condo's that causes their prices to remain depressed.   

But I also had the challenge of needing to educate them on the value of their building.

I believe the challenge will be finding a property that has an acceptable cap-rate.

It was around the end of September when Scott at Bigger Pockets announced a 90 day challenge.

I think the bigger the property the more professional you need to manage it, this could be challenging if you cant figure that out. 

13 Things to Consider When Looking For a Rental Home in GermanyMoving to Germany can be an exciting, challenging, and interesting experience for expat families living here for the first time.

I'm an out-of-state buyer and am wondering if there's anything unique to this market that I might be unaware of (eg. special certifications, etc). 

Hard money is challenging, but it does have it's place.  

I will also take the investment and occupier tax benefits as his low and fixed income won't need much tax breaks.Finding the right duplex that makes sense from both and ROI and location sense (not on "multifamily row" for example) will be challenging but I'm trying to see if this makes sense for me financially.