I've been a small time buy and holder investor for about 10-years and am now looking to supercharge this to build both a legacy for my kids one day, as well as a path to exit my W2 job.

Plus you get market appreciation as well.  

Hello, we are trying to buy our 2nd STR property in Kissimmee/Orlando area. we currently have 1 bed/1 bath condo in Kissimmee and it is doing well so far. ( been 2 month) I am wondering anyone has 2 bed 1 bath property?

Thank you again. check out the syndications and passive real estate investing section as well.

I'm sure it varies depending on the market you are in as well.

well, the good news is that your lender will be able to add back deprecation, mortgage interest, property taxes, property insurance, HOA dues and even some one time costs. 

They could go down as well.

The entity structure is typically different than multifamily as well. 

Well, that's why I said "is that legal to do".

Check references, screen well like a normal LTR tenant, if everything checks out why not?