This is merely the nature of the business. 2.  

Obviously my dad was the one with all the skin in the game but i knew I had a learning opportunity.

Condotels that allow short term rentals, are considered to be non-warrantable condos for the single fact amongst a few others, that they are transient in nature, similar to a hotel.

Quote from @Natalie Stanley: There are many ways to skin the cat.

Technically speaking, I am the only "natural person" in both entities. 

I personally own a personal home for the past 7 years so I kind of understand what can go wrong and things of that nature besides being a landlord, I never rented where I live just yet.i do agree with you, I’m still okay with going after a single family especially if it’s a great deal, why pass on it but, I do want to take it easy whether it is a single family or not, a duplex would still be a little considered easier compared to like a triplex or a quad. 

Do not invest in any city on Neighborhood Scouts’ list of the 100 most dangerous US cities.Low risk of a natural disaster: I frequently read of entire cities devastated by a natural disaster.

I was unable to get any deals due to the nature of the divorce process but now that is over and I am ready to invest flip, sell, and also buy and retain for BRRR. 

Unless someone has a large backing of investors, conventional financing will be hard to find for a project of this nature. 

I think you need a new accoutant, or else your financial situation is more complicated..A STR to me is still a rental....The nature of flipping is that it will be part of your ordinary income.