The bottom line is this: Concealment is not asset protection, proper (time consuming and expensive, I know) management, and good, prudent, practices (ditto), WHICH ARE ADHERED TO, and insurance (expensive), are needed for asset protection.

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!

I underestimated utilities in my early years, so I ensure those are properly captured (electricity, gas, water and trash).

If you used a loan to rehab your property and find yourself in a difficult position, doing a straight refi (just paying off the old mortgage) will be easier than trying to pay off the original loan and take additional cash out.

As far as the sale of a property with a mortgage on it, that all gets sorted out at close. ie, you bring your money, the bank gets what they have coming, the realtor gets what they have coming (if there's one involved) and the seller gets the rest.

But after all this time and effort, I still don’t have a proper syncing system.

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.

If you find someone giving you confused looks, seek a mortgage broker that helps investors.I'm not so sure how they would calculate income from short-term rentals.  

Answer sure.. have to check if there is a due on sale clause or if you have a PG to the orignal seller.. that mortgage stays in your name unless there is a formal assumption  Maybe the example is more challenging for a house as the property.Ex. with vacant land - seller finances to me $20k with 5% down and $1k/moCan I after 1-2 months, then resell the land to a cash buyer for $25k, pay off the original $20k and pocket the $5k?