Going back to ordinary and necessary - if you own just one or two properties and spend thousands on your clothing with your logo on it - may be a bit of a stretch!

Go knock on the door. 

My duplex will be paid off in two years.

You're also misunderstanding and heavily conflating some basic tax concepts.its either passive or not.Yup.If its not, its trade or business income.You're conflating two different concepts here. 

Then, the builders came from all over the country as South Tampa became the number One place in the US to buy Tear Down wooden houses to build Two Story Block houses and Townhomes, with 80% building square footage to lot size.

There have been way to many people who think that their STR is worth 100k more than the exact same house 2 doors down.

Although it will change, but I have 9 doors (including my primary) and I haven't put a down payment out of my own pocket since 2015.

First deal to get my feet in the door.

Hi,I rented out a room to two friends over the past 1.5 years and it all went well so I never had to really exercise evictions/late fees/ any other nasty things.

mixed use residential conversion of retail space to str units plus real estate office, two restaurants space tenants What made you interested in investing in this type of deal?