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..  

For those who already have someone working for them what did you find to be the challenge when training someone to take the job serious if working from home.

What are the risks and challenges do you see?

While the city council’s societal heart may be in the right place (for the tenants getting priced out of the Seattle) the onslaught of recent ordinances (1st in time application - challenged and overturned in Court, limits on move-in costs / pet fees, no criminal checks, etc.) these have in many cases encroached and/or completely ignored landlord/property owner rights and create such complex regulations that it is in many cases not feasible or cost effective for small mom & pops to manage their own properties, so they reach out to pros and pass the costs along to the tenants.

I guess my question to the group is have you syndicated in the past and with your first deal where did you find the greatest challenge?

Those are just the safe harbors; you can try to take the deduction without use of the safe harbors but the IRS may challenge it.With the "in service rules" you need to have the property "in service" in order to take any deductions. 

And as I suggested in my post above it was in the more challenging area of South Shore around 79th St.