It shows you're committed to growing your investment, and that’s exactly what a good property manager (PM) should be helping you with—they are stewards of your hard-earned money.I would suggest approaching the conversation like this: “Hey, I’ve noticed that maintenance expenses this past quarter seem a bit higher than usual.

This approach would allow you to use a 1031 exchange later to defer the capital gains taxes when you sell.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.PM us if you’d like to discuss this logical approach in greater detail!

I think that’s a great approach. 

Would love to hear different approaches, thoughts, etc. on this. 

I would probably approach your tenant with this information and say, "If that is the way you want to play it, so be it... but be aware you are really screwing yourself if you go that way" and explain that situation to him.  

Here’s how I would approach your situation:If you’re in the early stages of buying, you'll likely need to take the vacant unit due to existing lease agreements and oregon laws.

A bit about me:I live in Portland, OR (which is quite expensive)I’m a first-time homebuyerI’m interested in the "small and mighty" approach to real estate investingI’m actively contributing to my 401(k), maxing out my Roth IRA, and have $30K in savings.

Do you mean the "Healthy Homes Rental Inspection" program? 

So if I approach a listing agent and refuse a commission and the seller lowers the price, your position is that is a taxable event?