Ideally I’d be looking in Washington county on the west side if I could swing it. 

Eugene, I deal with a large number of room rentals.

Ideally this would grow and eventually give off enough cash flow to buy more when I get back to the states. 

The revenue is only count once it hits your Schedule E tax return, so you're riding the expenses until you file taxes.However, if you use an asset based lender (we have on one deal) they don't look at it through DTI. 

Ideally, if you're close with your contractor I would bring him along to showings to mentally tally a rough estimate of cost together (he may see red flags you don't and vice versa).

These would appear on a Schedule C (if it's a flip) or a Schedule E (if it's a rental). 

If it’s an upgrade def raise the rent over time to settle w/e he’s willing to pay.

Never took depreciation or upkeep/capital improvement expenses on schedule E but always claimed full rent income.

Make sure a contact name, phone number, and e-mail address are included on the cover letter.

I would guess the discount would be in the 10-15% range.Other considerations for you:  My ideal scenario is selling my rental to the tenant.