Are you serious? This 60 is awesome. I'm a firm believer in keeping the rig you've owned. The way I see it is like this, every time you make a repair or upgrade it's one less thing you. Red to worry about.
x2! That is a great looking FJ60, Brother. Like I said, and LeRoy alluded to, you'll get to where you want to be one step at a time. Every upgrade, every repair, every mod gets you one step closer. Better on your sanity and your wallet.
For what you ultimately want to do, the H55, gears and OME sound good - though you may not even need to change the gearing. I'm not particularly smart on that, so explore the forum and see what others have said about that.
When the A440 (automatic) died in my FJ62, that's when I had a decision to make. Try to rebuild it, swap in a new one, convert to an H55F, or do a 5.3L/4L60E swap. Rebuilding it wasn't really an option, so I first looked into the H55. That would have easily cost me upwards of $3K to source the tranny and convert my truck to a manual (adapters, clutch/pedal install, etc). When it was done, I would still have an engine with 255,000 miles on it and a tranny with zero. So, I opted to put the money I would have spent on the transmission towards the Vortec swap (and when most people talk about the swap, they are also talking about swapping in the GM transmission - typically the 4L60E - with the Vortec).
While the 2F and 3FE engines are fantastic - my 3FE was super reliable and probably would have given me another 100,000 miles - they are underpowered (as you know) and parts are getting scarcer. You can source parts for Vortecs anywhere and the base 325hp gives you passing speed at 70+! If you plan to spend much time on the highway traveling from the great hub of Denver to all of the wheeling/camping spots within a half day's drive of you, you may appreciate the better behavior on the highway and the improved gas mileage. You won't be sacrificing any trail performance, either. I upgraded my tires to 33's when I put the OME kit on, and with stock gearing I run 2100 rpm at 70mph. If I were going to be no-kidding rock crawling often I might consider switching to lower gears, but for most of the fire roads and trails I'll see my 4.11s are fine.
If you want to seriously consider the swap, PM me and we can talk more about it. There are lots of older threads on here that document in detail many of the early builds. Mine is one of the most recent, and due to the number of pioneers on this forum who have contributed their experiences, the availability of parts for the swap, and what I think are cheaper prices for some of the parts than before, I think the Vortec swap is easier and more affordable than ever. @FJ60Cam did one of the most popular and complete swap threads, so read through his as well.
Good luck to you; do what's best for you, first and foremost, but I hope you thoroughly explore keeping the 60 before deciding to go another route.