So, do you have any advice for a first-time house-hacker wishing to jump into the appreciating deep end and swim with the sharks? 

One of the primary challenges they face is navigating the market without trustworthy contacts. 

But like Patrick points out, each city has their own processes and some have point of sale violations, and Cleveland is supposed to start doing this in the fall, so the best thing you can do is to find an experienced agent / broker who can help navigate these issues with precision and ease!

Consider consulting to navigate tax implications and proper structuring.

I find that if you are able to help people within your network navigate the complexities of private money, they will be less apprehensive and less likely to ditch you at the funding table because they get skittish.

I used to work for the VA and I know for a fact that the VA loan will allow for additions, if nothing else, for handicap access and disability related navigations of the property, to include stairwell modifications, handrail additions, etc.This is usually only for unique cases of disability though, IE severe injuries and/or disabilities.

Bad news is you still have to pay them to run it for you.Hope that helps navigate the seas on a surface level for your NOLA STR!

Deal shark swimming through the dark cold waters.

I have included a BiggerPockets article outlining BRRRRs and navigating leverage to scale your portfolio below.

STRs are very hard to learn and navigate.