The rent range is pretty wide for that property however and your estimate is on the higher side it looks like, so maybe just get a little more conservative there to be safe, but even at $1300/month rent it still cash flows decent.  

I drove by the other day and saw one of the windows in a unit wide open. 

If the conviction is old and your record is spotless since you got it, it will be harder for the landlord to reject you.https://www.nolo.com/legal-encyclopedia/question-r...Oregon just passed state wide rent control.. and its either passed that you cant now run criminal.. or they are trying to pass it.Myself I would not care if it was the law or not I would run it.   

Bend getting pretty populated but outside of town there are still plenty of wide open living.

If it is not in compliance with the historic district that may be difficult to work around but not impossible.They may require an architect or structural engineer to evaluate the building and provide a report.This could be a great opportunity for you, just walk in with both eyes wide open.  

Taxes are not that high and place should be renovated to a certain extent already, so I hope that all makes it work.

You can struggle through life using spreadsheets, but as soon as your hobby becomes anything resembling a business, or you can't remember everything in your head, double entry bookkeeping is the world-wide standard. 

These e-signatures are signed after she passed which was not long after they came and I stalked the solar panels with out anybody but her being home the extent of the documents I found in the Gmail account go as far as claiming she signed off for the inspection from the city.

The usually do city wide reassessments when they need to raise tax revenue or simply adjust to reflect market prices.

Your local Realtor Association will offer a wide variety of courses - many online - for you to chose from.