I am going to get hit with capital gains and state taxes(Idaho 5.8%)..closing on cabin on the 18th of Nov.

*I am not a CPA, tax professional or a lawyer*I cannot give legal advice, so all of my advice is illegal advice.As far as I know, section 469 of the tax code is what allows for the "STR loophole". 

I can get the info from the county tax records but still need to take another step?

Here are the numbers I know so far:Rents4 units all currently occupied on one year leases- #1: 1/1 $995 monthly- #2: 1/1 $995 monthly- #3: 1/1 $995 monthly- #4: 2/1 $1,100 monthly- Gross rents: $4,085 monthlyExpenses- $12,070 taxes annually- $350 monthly insurance (my estimate, they have liability only right now)- $175 monthly landscaping- $120 water (electrical on separate meters, tenant pays)- Total expenses: $1,651 monthlyNOI around $2,434 before vacancy, maintenance, and management (although i would likely self-manage these)Property needs about $50K in other repairs and udpates from what I can see.

Cody,It is not easy with low down payment and  with current prices, property taxes and rates to live for "free" these days in most of the country.

Insurance claim has NOT been paid.

But didn't find anything to my specific question.There's a real estate agent claiming he has an all-cash buyer for one of my properties.

Holding onto it is a smart decision, and you're entering property investing in a solid position.To get started, focus on ensuring that the rental income will cover your mortgage, taxes, insurance, and any maintenance costs, leaving room for profit.

I’m trying to have him see the bigger picture if he puts money in tax advantage accounts first and strategically uses a tax professional, that he will be able to offset his high tax bracket w2.

In fact, you’d have no choice but to claim material participation because that is exactly how the regulations read and require.