Maintenance was averaging $300-$500 per month because I was useless in solving any house-related issues (never having done any maintenance myself before).

Have your Insurance Agent do a quote for this with one of their companies that runs "CLUE" (claims Liability Underwriting...) reports. 

@Matt M.It will be hard for the HOA to fix without funds and although there may some personal satisfaction from doing this, it will not solve or help to solve the issue.

My fear is that when I get the distinction of living through my first IRS shakedown I'll be creating more problems for myself than I'm solving by keeping my accounting simple and minimal. 

If you sell a house with a problem to solve they are going to want to be compensated to solve that problem but if you are ok with that then it may work.  

Well, if the numbers are as you stated AND it doesn't have any upcoming needed CapEx, it sounds pretty reasonably priced to me (esp[ecially compared to Portland).However, have no clue what's a avg RoR in your neighborhood to say good/bad. 

The clue report will stay with the property no matter how often you switch companies. make sure you’re only claiming “disasters”  I use a $2500-$5,000 deductible as it saves more than $100 per property per year and I’m obviously not making a claim under $10,000 anyway. with 14 properties this aves me $1400/year. 

It doesn't solve the problem but can help to address it quickly and charge the guest for such violoations.

You could perhaps try and fix that problem and offer some kind of a cash for keys option (less than your first offer) and also pay for a full service moving company to solve their problem of packing stuff and also moving it to their new location.I hope something works out in your favor on this one, sounds frustrating to say the least!

We are paid directly in proportion to the problem we are solving what i learned.