Have you incentivized a GC with bonuses to meeting or exceeding cost/schedules? 

I feel like a few items, like guest count, amenities, nightly cost would be pretty easy to manually snag data on but what about occupancy rate?

I realize that they were just trying to sell me something at all cost and been chasing me with phone calls/text messages.On that note, I wouldn't mind to have someone more experienced than I am to run my deals through and pick their brains from time to time.

Question: Is it worth it to perform a cost segregation when you rent out spare bedrooms ? 

You will have fairly sizable tenant improvement or build out costs with each lease.  

With housing prices skyrocketing, the increasing cost of raw components and lumber, and labor shortages, the idea of owning a piece of income property is just not in the cards anymore for many individuals.

I really do try my best to be an awesome landlord, but it’s starting to not feel worth the time and energy.The house is at a 2% fixed rate so it’s hard to consider selling (at least right now), and getting the tenants out of the house would cost at least $5k per the Portland laws.

lower the size of your unit and therefore your build cost per unit, your sale price will go down but focus on density and get familiar with zoning and what your city will approve. my best suggestion is to do it in downtown districts where there is unlimited height and unlimited floor area and you can build every square inch of the property and reduce parking because of proximity to transit. property values are higher, rents are higher in downtown markets, there are just too many economies of scale compared to suburban deals.

I don't have a comprehensive experience  but I tried to find the least costly one for every step for me and applicants/tenants.

What all are common items included in closing costs on a wholesale transaction?