Me personally, the risk of disrupting that by trying to make them pay for it outweighs the gain.

However, I would be delighted to gain workplace experience-say two years-prior to furthering my studies.

Leverage REP status to use other losses against capital gains in the liquid assets of the company (invested in EFT's, etc)The policy for loss distribution would be:-All must be active (preferably material) participants to get deductions; hence the 20 or fewer so relationships can be maintained-Non-REP's can take up to $25k/y as PAL.

My first filter would be comparing the cap rate of the property [this is basically the operating margin of the asset] with your weighted average interest rate [ for example if you borrow $80k @ 3% and $20k @ 9% your effective interest rate is 5%] If your effective interest rate is higher than your Cap Rate, the investment doesn't make sense, at least in the short term.

I like Roth IRAs, and researched a lot on the Roth 401K and Solo 401K, I am aware of the IRS rules when it comes to my Self-Directed IRA, which I intended  to use to do Real Estate Investing. but I am more interested in keep most if not all of the profits I earn and not pay Capital gains and other kinds of taxes. 

I do not think the PF/Gatlinburg area will go back below 80% occupancy as the area has gained so much momentum during COVID.*** There hasn't been a low month in a long time!

This implies that you basically are going to have a heavy weight (the insurance company) in your corner in any suit.One umbrella policy can protect all assets.  

But for your income property, they'll give greatest weight to the income method (the one based on NOI and cap rate as you said), as they should.You wrote "NOI divided by the Cap Rate" but keep in mind, the appraiser will use what they feel is a market cap rate, not the cap rate when you purchased the property or a cap rate you want them to use.

He said that the entire purchase price could be deducted from income, thus offsetting capital gains from other (ie, stocks) sources. 

Based on the limited information you posted, and assuming the property has gained in value, I would sell and find something with a better return. $183/month on a property that rents for over $2k isn't enough cash flow in my world.