I had to be certain this deal is DOA because there is always that one person that see potential in deals most people would pass on. 

Potentially get a commercial loan or HELOC against the properties to fund additional deals.Future: I will have all the debt from the prior renovation paid off this year from the rental income.

It can be seen as a unique amenity that sets your property apart and attracts potential renters.

Joe, I can say that a lot of people avoid the West End/Portland areas, but I believe those people are short-sighted or unable to see the potential in these areas. 

If you have experience investing in this area of the country and can shed some light and insight into taxes, insurance, Airbnb options (easy/hard/impossible), permits, flooding, other potential issues, etc., I'd be most grateful!

The lenders that get a share of your property are potentially the same ones that would put into the Reno costs?

The entry-level Quickbooks Online software itself is expensive $250/yr... that's not even adding up potential books/courses, CPA fees or personal tax filing software like Turbo Tax.

The three most common approaches include:Cost approach: An estimate of the replacement cost less depreciationIncome approach: Calculation of estimated potential rental incomeSales approach: Uses comps of recent transactions on similar propertiesBe sure you are leveraging the tax incentives availableIdentify any applicable tax incentives available for commercial properties - historic tax credits in certain areas, opportunity zones, environmental sustainability, etc.Understand available tax deductions, credits, and rebates - Tax deductions decrease the taxable value of a property, tax credits directly reduce your tax liability dollar for dollar and tax rebates are a refund of taxes paid under certain conditions.Utilize a cost segregation study - Cost segregation allows you to reclassify assets into categories with shorter useful lives, therefore accelerating depreciation and creating tax savings.Leverage energy incentives and deductions - Look into the Section 179D deduction and how you can save on tax by meeting certain standards to make your property more environmentally friendly.Best practices for commercial real estate owners and monitoring their property tax regulations:Plan proactivelyWork with a professional to receive guidance on complex regulationsUtilize specialized software tools to drive efficiency and compliance.What questions do you have regarding property tax valuations?

It also sounds like you enjoyed the hosting process and the communication with your guests and potential guests when you were handling your bookings yourself.So I say why not take back control of your property's bookings, get back into the game and save yourself some money? 

I thought that the ability to work "whenever I wanted", and the commission potential and income, would help me get the basic funding needed for when I was finished with college.