Starting out in real estate (passive long term vs short term)

[Jacob Fafard]

Hi guys first post in the forums, forgive any naivete. I'm twenty eight currently working as chef who "likes" but doesn't love what I do. After listening to almost all of the forums I'm quite convinced this is what I want to do in some capacity. I have 8 years experience working construction for my father's construction company. I understand the building/contractor side but lack some in the business aspects. My question is are there any professionals out there who can give me their perspective on a newbie starting out in short term rentals IE(VRBO and Airbnb). 

I've got a decent understanding on how long term (passive/semi-passive) rentals work, however I want to transition into the real estate industry full time and feel as if short term rentals will create a better platform for a business. 

My idea is to start with one property, maybe even a tiny home. Once I've gained knowledge of overall management, price optimization, systems for high turn over and overall understanding of this "niche" part of real estate; I want to scale the concept to other properties and also manage other short term rentals. That being said I understand that the short term rental market right now has a lot of grey areas. There is always the risk that that area could change regulations and take away the business in a second. Meaning all properties purchased must cash flow as long term rental as a backup. Do you think tiny homes being portable hedge my risk? Should I stick to homes, with the possibility of a rentable ADU or condos?

I understand its a lot bottled up in one question but would greatly appreciate any and all's advice regarding the matter.