I know in my area they can require it, and we are nowhere near as strict as NY. 

But I find from personal experience and from my buyers' Airbnb experience that it's a bit of a hassle trying to get guests to rebook at the new listing.I don't know how strict Joshue Tree is at enforcement, but in Denver and Colorado Springs here, you could probably get away with an STR listing for three months without the license.

Since you’re considering converting the upper unit into a short-term rental, you may also want to implement strict rules around smoking or strong odors in your house rules to avoid future issues.

Timely because January 31st is the deadline.Sending 1099-NEC (formerly 1099-MISC) to contractors and vendors2024 update: While not directly related to sending 1099-NEC forms to your contractors, you may have seen the panic on social media about every $600 electronic payment reported to the IRS under a new law.

Yea this is a long-term personal play more than a strict STR deal. 

As I said earlier, this is strictly for investment purposes.The property does not have to be turnkey, if there is room for improvement that's of no concern as we both have the skill set to invest in whatever upgrades are required.

This vary heavily town to town. 20% down is great if buying strictly as investment but if you have a way of owner occupying I would explore that route and apply the 20% down to increasing value of property and instead using low money down loan. 

@Matt WeddonLegally, you’re covered as long as you stick to objective, non-discriminatory reasons for rejecting someone (things like personality or ‘vibes’ don’t cut it in Fair Housing law).

Or do I need to do it strictly as an investment property? 

As a new owner, you should confirm if you can raise the pricing on the rent, and do that accordingly to the laws.