I have some questions about the material participation rules for the STR tax loophole.

Given that you've owned them for almost 5 years, there is also a good opportunity to do a cash out refinance and obtain tax free money that you can use to expand your portfolio even further. 

When evaluating rental properties, aside from school districts and convenience, consider factors like neighborhood amenities (parks, restaurants, shopping), rental demand, job market trends, property condition, potential for appreciation, and rental income compared to expenses (including taxes, insurance, and maintenance).

Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed.

From there, once you get under contract, get your 203k consultant in the property immediately to do their inspection/schedule of repairs write up.

@Tracy Derickson Click on the Build your Team tab and you can find sponsored vendors for tax and financial advice here on BP.And as @V.G Jason stated give us a fact set and you will get free advice on your case on the forum. 

You can just give that statement and your spreadsheet to your tax preparer.Trying to add your paid expenses to PMC software is almost impossible, as it will misrepresent what the PMC actually did.Another option is to just send the bills to your PMC and ask them to pay from your portfolio balance.

We are an LLC, taxed as S-corp, with K-1s.

You don't need W2 income, tax returns and no one is looking at DTI.

I used to work in consulting for the robotic division at DHL Supply Chain.