This is part of my loan process - a discovery and strategy session with the client to understand their scenario, future plans, and overall situation so I can structure the loan to fit into it. 

It is very common for residents to note of issues within a week of move-in.  

There is a lot of great advice here that I will keep in mind as I look for my first house hack.Your New Bedford example is a scenario that would be great for me.

@Mary Lopez It definitely depends on your scenario and the details.

So far I have gotten good feedback and I think the best way to learn is by doing and by learning from real life scenarios.

It is a common area for investment property.

Quote from @Chris Mason: Rather than starting with one lender and going back to the tenants, another approach would be to work with a commercial mortgage broker who will put the full credit package in front of 10 or a dozen lenders, and see what they come back with.For example, for scenarios like this, I've seen lenders come back and offer a new loan that has a maturity that's coterminous with the lease.

What are some common issues you faced, and how did you resolve them?

its pretty common .. in the PNW there are large communities and this pattern happens more than one might imagine..

No way, unless you're talking about a multi-family common area.