I think the best bet is to obtain the rental license as well as the commercial activity license that is necessary to apply for the rental.  

We recently had a rental property where the unit needed re-painted and the carpets needed professionally cleaned multiple times to even get the smell out; which your best bet at that point may just to be to replace any carpeting you may have in the unit. 

Your best bet is going into small multifamily, and going for the low money down. 

I’ve seen a bunch of posts here over the past six month on BP where people seem to be betting big money (some call it investing) based purely on someone’s charm and word.

I  bet you will lose 1 tenant  only 

@Becca F is a good example of that in her big post.Your better bet is to go after a really high quality properties--maybe not Cali--but other areas like Tennessee, Carolinas, pockets of Texas, etc., if Cali is too rich for you.

It can also be safer to diversify your investment properties across the country.

With it being such a unique property, I bet you'll start getting repeat customers and as you build up positive reviews and the same people start booking it again year after year, your schedule will fill up more.

If your goal is to become financially free quickly, your best bet might be to sell and buy something you can house hack but if that isn't an option, keeping this house rented for the next 10 or 15 years could essentially retire you so long as you can find a way to avoid losing half of it to taxes. 

I didn't see anyone mention the Five Point neighborhood, so I am going to guess this is a relatively unsafe bet?