I want to stop being pennywise pound foolish and get things set up properly. 

We network with other fix & flippers teaching them how to properly structure a seller financed note so that it has value on the secondary market, we then buy a partial from them to take out most, if not all, of their cost basis so they can recapitalize and go do another deal. 

BUTTTT there is sooooo mcuh garbage out there that you'll have to sift through to find the gold and then you have to learn it, put it in proper order, THENNNN take action. 

Consider different strategies like mid and short term rentals as I believe the Portland area would allow for success in both (although I have heard Portland proper is tough on STRs).Best of luck!

Leverage technology early and put everything in the cloud, so you can access info wherever you are.Make sure to get properly licensed and obtain E&O Insurance.

I could see fully comping 1-2 nights at low season rates, particularly if one doesn't have a lot of reviews yet, but would you, as an established host with tons of reviews, comp a full week or more of a prime season stay? 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Two weeks later, 5 bottles of Pepto 8 nights of no sleep.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

So grateful you introduced yourself.. what's the one burning question about investing that keeps you up at night?