Don't discount that.Real estate remains a valuable investment despite current challenges due to its tangible nature, long-term appreciation, and potential for consistent rental income.

If you do, you should expect a very aggressive challenge by the IRS.At $350K of combined value it might be worth the cost to get a segregation study if you intend to keep these a long time.

The existing number of vacation rentals are so far over those caps that anyone who gets on the wait list today will likely wait 5-10 years before they're up for a permit.I do think this is the natural progression of what is still a relatively new industry.

Challenges?

Heating costs go up in winter, as does electricity due to the reduced natural light and more people indoors.

Beyond that it's not in my nature to complain; I just like to identify problems and solve them, and if I can't solve them then either accept them or move to greener pastures.  

Challenges?

Challenges?

This may be part of the reason why some decide to quit pursuing real estate investing, especially when challenges start presenting themselves.

It’s always fun to hear what challenges new investors tackle.