If I want to go from Hollywood N. Perry (HWO) to Tamiami (TMB) Do I have to
file a IFR flt plan if I want to go IFR. Is it possible to pick up a (local)
ifr?

I'm not sure I understand the question. To legally fly under IFR in
controlled airspace (which you will be in), you need an IFR clearance,
which means filing an IFR flight plan. You can do that beforehand ("the
usual way"), or you can depart VFR (weather permitting) and then try to
get a popup clearance. Getting a popup generally involves filing a
flight plan in the air. It can be done through approach if they are not
busy, but they may tell you to contact flight service (on the radio) and
file it there, and then wait until approach gets it.

If you have plenty of VFR weather while you're doing this, there's
usually not a problem. But if the weather is closing in and approach is
busy, you are taking a risk that they can't take you in. Then you're stuck.

If you already know this and are just asking the likelihood of getting
stuck on this particular route, then I don't know the answer.

Jose
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