If your income is below the $150,000 AGI limit you will be able to use up to $25,000 of the passive losses (if any) to reduce your income and therefore tax. 

I'd bet that for the last 50 years, investors looking at Boulder have felt it was unaffordable, and that the numbers don't work for investors.

While I overall agree with you, there is a case to be made that premiums will start to normalize:Namely, major insurers pulling out of the high risk areas like FL and CA are limiting their catastrophic events.  

While the self-directed IRA is a great structure for investing into real estate and other alternative assets, the Solo 401k is widely considered to be even better.Compared to an IRA, Solo 401k contribution limits are roughly ten times higher and there is no custodial requirement for the 401k.

In fact, there are even financial markets that specifically bet on future levels of the Fed Funds Rate (unsurprisingly called "Fed Funds Futures").These futures correlate very well with certain bond yields which, in turn, correlate very well with mortgage rate movement.

Knowing this on the front end limits any exposure to major fluctuations on deal terms once submitted.

What if I were to tell you the Investor A triplex was sold two years later for a $100K profit whereas Investor B is run down and exhausted from managing their four "C" neighborhood single family homes and when investor B goes to sell,  they can only attract break even offers because the only buyers who would step to the plate were investors who were not willing to pay retail with so much distressed opportunity available in the "C" neighborhood due to limited barriers of entry. 

Between forced appreciation on general improvements on the property and the capacity to add an additional residential structure, the sky was the limit on value growth.

That said, it could be that the location of your property has some sort of local ordinance that has a 90-day limit, and Airbnb is simply following that.

Do not go and invest out of state because people come into the forum and try to convince you to work with them on these goals (so ridiculous), you aren't ready for that and you have a good foundation somewhat locally.Your best bet, if you can't move, is to keep investing outside of New Jersey and stay close to your current property.