I am not sure if I can help you or you could help me .

The software needs to help with accounting, deposits, repairs, etc. 

We spoke to the lender but they weren't much help beyond saying "you've got to find a way to pay the 137K".All thoughts much appreciated.

I know everyone will be biased toward the strategy they prefer, but I want to hear from those successfully generating income from STR specifically.What books did you read to help you start?

Maybe I misunderstood him or he meant something else, but I don't see how paying the same amount it would be regardless but just in 3 separate payments helps reduce the mortgage more than it would've been over time.

I would love to offer as much feedback as possible and help you all optimize.

"Long Distance Real Estate Investing" by David Greene is a good options and will help with getting an idea of good markets all over the place, not just your own backyard. 

Having an experienced agent on your team before the rehab i think is very important because it is during the rehab when they can help add the most value by pointing you in the direction of what adds value to the sale, what finishes to choose and what to avoid, even what color paints are a good choice, insuring that your target sales price is not just realistic, but that it can actually appraise for that amount. 

They offer some great oregon-specific forms that can help you stay compliant and organized.

Tell them if they have any clients considering buying an STR, you would love to help if needed.