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.

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 a common area for investment property.

People thankfully aren't stupid and have common sense.

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..

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.

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.

Should I offer to pay them for their consultation, or are these types of questions common as part of the PM vetting process and is a "courtesy service"?

I will also be tracking expenses related to repairs, maintenance, travel to and from NV, hotel stays, meals, gas, and other regular business costs.In the long term, I aim to purchase additional properties under the business name, but I understand I need to establish at least two years of income and credit history before doing so.The issue I’m encountering is that my accountant has not provided any guidance on how to structure this scenario.