Chris, I haven’t used First United for a duplex, but do have experience working with them on traditional mortgages and to be honest I’m not surprised they got their info wrong, their knowledge and customer service isn’t the best (and their website isn’t user friendly at all) I would definitely talk to other banks.

I bought my first primary resident home in my early 20’s.

If you are planning to buy a property as your primary at first to house hack (owner-occupied), then the underwriting gets more lenient in terms of ratios.

This home was purchased with FHA and will be his primary residence.

This home was purchased with FHA and will be his primary residence.

We're not sure we will be able to find  traditional financing through a bank for it.

You can do so with a cash out refi on your primary res if available.

"No check issued".) 2: Would it behoove me to achieve my write offs this year (the year I need them) and quitclaim the deed from my LLC. to myself, converting it into a primary residence down the road (adjusting my basis with the improvements and repairs) and only allowing potential litigation to attack my free and clear title for this short period of renovations vs. the life of our occupancy at the property? 

Not a tax advisor, but generally pretty simple.Once you take a member draw into your personal name (post-tax), you can do whatever you want with it.If you're buying RE in an LLC, I'd be sure to keep them in a separate LLC from your primary income earning activity that produced the cash.  

If you're looking to invest for cash flow in a traditional long-term rental, you're probably best looking in the midwest somewhere.