I would evaluate those instead of "stretching" for a rental at top dollar.

I was watching a webcasts and the presenter mentioned loaning money to landlords "stretched" for the purpose to make a "big" repair and charge 20%.

Saying it caused it, that is a huge stretch to me.

It'd be great if I didn't have to stretch it out to 2 years just because how much I'm itching to take off, but the future is always unpredictable and I should definitely be good financial standing before I get ready to take on this journey. 

Stretching the amort to 30 and not having to worry about a balloon did a lot to offset the initial fees for me.

Yes, the Portland area may be a little hot but there other markets in which your 20k can be efficiently stretched.  

Another option I guess would be to begin investing now to gain passive income to help pay debt off, but this seems like a stretch with the amount of personal debt we currently have.Thanks

He says he will pay at the end of the month and knows I expect October's rent at the beginning of Oct, but it seems him coming up with $1,000 is a stretch.  

Maybe if you had MFH... but SFH that's a stretch. 

The goals I set are meant to stretch myself, because I will need to skill up in order to achieve them.