Do not apply with the first list of items. Those are related to PR and certainly not related to TRV.
The second list is more in line with what you will need, however, having property in your name in Florida isn't going to assure them you will return to the Phillipines once your 'visit' is over. Instead, include proof of the property you currently own in the Phillipines and also include a letter from your boss (if you work) stating that he/she is expecting you back on xxx date, or if you can't get that, include your pay stubs to show your ties to the Phillipines. Show them proof of funds that you have enough money in savings to support yourself while you 'visit' and also a letter in invitation from your boyfriend and a statement included therein that he will provide for your necessities while you visit will definitely help with your case.
If you include all of these things I see no reason why you would be denied a TRV unless you have a criminality issue.
As a side note, you keep identifying yourself as Transgendered, however, you have not stated if you are post op or pre op. If you have not yet actually gone through the physical change, then CIC will view your relationship with your boyfriend as that of a gay relationship. If you have already undergone gender reassignment, have you had any of your other documentation changed to reflect that? In that case, CIC will need an explanation from your boyfriend, as stated before, about the nature of the relationship and that he is aware of your status and such. Without a letter from him in this scenario, they may feel you are trying to 'trick' him and that may cause a huge delay in your application.