I highly recommend that you have a Maryland attorney review the lease and make changes as it pertains to the laws in Maryland before you start using it.  

It is probably cheaper than joining the apartment association and they would have the means to qualify a new tenant (credit, criminal, rental history, income) and ensure that the tenants are signing a lease that follows the laws in CA. 

But I don't practice law in this area so I would suggest you talk to someone more knowledgeable.

Been reading a lot and it does seem like the numbers regarding cash flow for a single family home on Maui (right now) wouldn’t work too well.I understand and accept that passive income is for the people who’ve built a massive net and are at the top (but even then I think they have to work and make sure their system stays functioning)I really want to learn more about owning/operating vacation rentals, specifically in HI if possible and specifically the tax part of it (now with the shift of the 2018 tax laws).I’m going to dive through the forums and try find more books on the topic.

In my area just a ground level entry door for the 2nd floor unit would be acceptable so long as the bedroom windows are minimum egress size (5.7 sq/ft and at least 20" wide) and they are not above a certain height from the ground (I forget the exact distance off hand).Your laws are probably different though. 

I'm just afraid that it might overly clutter the ads/signs/letters if I need to adhere to the strict guidelines set by the Real Estate Commission around advertising.I will of course speak to my broker about this, but wanted to check what others have done. 

But if you want to set up some “tiny house vacation home” then it’s probably more “fun” than a strict “investment”.

I am only allowed to fill in the blanks. strong lawyer lobby there in IL... holy cow... but hey you just have to work with what your state laws are out there.. so it sounds like the original question the person needs to have a lawyer 

They post most of the new laws when they get posted and helpful information. 

So, as long as you are not refinancing your primary property you don't have to worry about this law.