@Sainath Muntha Yes, this is why creating complex entity structures like this is cumbersome and expensive to maintain. 

If you dream of owning on the Coast be very cautious of regulations against STRs, most communities are not STR friendly and some towns have revoked STR permits (lawsuits galore on that), so talk with an Oregon Coast based agent who KNOWS STRs or you could end up with an investment you can't rent and just have to wait out all the expenses of ownership until the appreciation kicks in.

People doing 1031’s of paid off properties for replacements that are only 20-30% more expensive.

I would definitely encourage you to minimize some of the elevation changes, it is going to get expensive quickly they way you have it shown.

@Angelo CortezMost STRs report income and expenses on an IRS Schedule E (not Schedule C) unless your STR is offering "substantial services"-> for example, concierge services or a butler to guests. 

Putting aside the fact that it probably makes more sense to get my start somewhere relatively local to me, I was still wondering, for you fellow Canadians (@Marie Shaug , @Roy N.) who have some experience investing cross-border real estate, are there any resources you could point me towards that would help give me an idea of what kind of additional expenses, taxations, or other considerations I need to take into account if I end up going that route?

Yes, additional expenses for MTRs include utilities, wifi, landscaping, consumable supplies you provide for your tenants, additional insurance needed for a furnished home, and if you are hiring anyone to help with the property if you aren't self managing.

However, the bedrooms do not appear to be over plumbing below so that might be very expensive. 

for example if I have a property rented for $2000 a month and I charge 1 month rent as a turnover commission and 10% of each monthly rentals as a management fee I would send my owner a 1099 for the full $24,000 and they would just line items the turnover commission and monthly management fee as an expense on their schedule E , correct? 

And remember to use a contractor who knows & understands the 203k and has strong financials to afford the start-up costs and ongoing expenses associated with 203k rehab projects.