I never owned a bike with boards but I have ridden them, I just couldn't used to them, my fathers deluxe has the engine guard and the highway pegs, they were comfortable on the highway but any time around town they weren't practical having to lower my feet to shift/brake all the time, the sitting position just made my back hurt and feels really cramped, now I haven't spent days on a bike with boards with im not really sure that I could. I like the look of them but comfort is more important.

 

I suspect you would benefit from have a much higher seat than stock, which would put your backside and knees at a much more comfortable level. That would help regardless of whether you use foot boards or pegs.

 

This.
No point in contemplating mods until you do ride one and then decide to buy one is there?
Then, you'll figure it out.
That is part of fun and challenge and part of customizing it how it will best fit you.

Oh and BTW, there are lots of guys your height who have probably done exactly what it is you want to do.

As far as riding a bagger goes, it will be much different than your softail.
Not as nimble, but lots more comfortable.
Again you'll figure it out that is if you ride one and decide to buy one.
I suggest renting one for a weekend when you can.

 

I have ridden one in stock form, not comfortable to me, I was going to order it with the mods done (bars and pegs) everything else I will do, I have sat on lots and ridden one of my buddies 2014 street glide special, I know the bars have to be changed no matter what, the bend in them is not right for my wrists as ive broken both hands, writs and arms and also my collar bones and my back, which is the reason I cant sit in an upright position with my legs bent for long, back hurts and the bars need the right bend so my hands are inline with my arms, as far as height I just like it, more comfortable.

 

I was considering this too but I like a low seat like the barebones on my night train so I have the feeling that im down lower in the bike instead of way up on top of it.