You would want to see a couple of the last jobs he did.

I have excellent FICO, really good income from full-time exec assistant job and lucrative but inconsistent part-time modelling and wanted to invest in 5-6 interesting properties.

@Mathew Wray  all though I do think Bend you have to be cautious there are no real jobs there and its heavily dependant on CA and Portland retirees who for some reason think its a great place to live :)  too cold for me.. and to remote.

Good job.

I apologize up front if this post is disorganized, but I'm sure there are other people who are or have been in my shoes and can offer guidance.About me: mid-30s, high-paying day job, telecommute and somewhat flexible hours, married with kids, own a duplex in Los Angeles county. 

My day job is partner in an insurance and tax accounting firm. 

Have you taken any bids from contractors on similar jobs and compared item cost? 

Then you don't have a way to get anywhere, do any repairs, go to a regular job.

I have a W2 job that pays decent, I could afford the mortgage.

So if you have reliable personal income, cash flow and can lower rent and break even, keep an eye on your property and your tenants, and you keep personal borrowing under control you should be able to do fine with rentals in an area with jobs.