Good post rick, you clearly explained where you're at and where you want to go.

I'm 6' 240# and I love it.  4000, you can just about get a new one.  The bike runs out of breath somewhere over 80, but until then you better hang on.  Seat comfort varies for different people, we have many mod's for it.  Many ways to skin a cat.  Some even say it's fine the way it is.  There's extended control to stretch your legs out with and the bars are the same size as harley's so go find yourself one.  Just make sure he ain't looking.  

If you're near anyone, check the savage rider map, I'm sure you can get some personal advice and a sit from our long timers.

And I'd say it's pretty reliable.  I've had 2, both started with around 15k miles.  1st one is at 45k and I'm gonna replace the cam chain and some other stuff.  2nd at 30k, and still ticking.  Fairly easy to work on, if you ever worked on a Vdub, it's just like that only better.

Just wanted to add a little to the already mentioned exhaust carb/issues.  The stock muffler does make the bike sound like a sewing machine and changing that out for a very reasonably priced sportster/dyna muffler will give the bike a really nice sound along with better air flow.  
The factory does jet the carb very lean to start with, and when changing the muffler, like with an HD muffler, the increased air flow will lean the fuel/air mix more; so a rejetting/tuning of the carb should be done.  This will aid engine cooling and improve overall engine efficiency considerably and add a nice bit of power.
There are Savage/S40's that have had a muffler change and a well executed rejet/tune of the carb and the result is a bike that will run very well, sound great, and have good power all the way to a top end well into the 90+ mph range.
My son recently purchased an '07 S40 which is stock except for a muffler change and rejetted carb and it runs great, sounds great and tops at 94 mph with me sitting straight up.  I am a weight watcher also and am in the 194 lb range currently...shooting for 165.

By the way, a new "take off" HD muffler, new muffler clamp, jets for rejetting the carb, and header gasket can all be had for less than a $100 so making the change is pretty cheap...just involves a little quality time for you and your new bike.
And like mentioned, there are really good used bikes with very low miles to be found for $2-2500.  This bike is a good deal and a great ride.

Good bike.. easy maintenance only a single cylinder and belt drive.. fun to drive good handling.. decent low end power.. much better than a 250.. not as good as comparable similar displacement v-twins, but makes up for that in the fact it's much lighter than similar v-twins.. the HD exhaust is probly what you need for a better sound without being too much louder.. I have the jardine, love it, but it's very loud unless i'm very easy on the throttle(when passing cops).. I like loud though, keeps me safe.. and visible(audible).. not alot of aftermarket accessories designed specifically for the savage.. but lots of modders on this forum that have come up with creative solutions.. many of the accessories for the other boulevards will fit the savage and people on here make accessories for it they sell like forward controls.. lots of how to's on here..

Just playing the Devil's advocate here. You're getting all the Pro's but there are some Con's too...

$3- $4000 will buy a lot of good, but different bikes. Craigslist is full of them for that price around here. The Savage is very simple and dependable. No doubt it's a good choice, but not necessarily the best choice for everyone. It'll have no problem pulling you, I'm 205 right now and it scoots! The smaller Hondas are kinda known to be a little on the puny side for performance, so the Savage should feel very similar. Pound for pound, you won't find a better bike for the money. A good used Savage can be had for $2000 or less & that leaves room for plenty of modifications. I guess it depends on how comfortable you are with doing mods. The info and friendly folks here will help you through them no problem.

The Savage is on the small side and feels cramped, in my opinion. Forward controls will help you stretch out, but that don't make the bike any bigger. The factory seat is awful. It leans you forward and crowds the "boys" if you know what I mean. For bigger guys like you and me, a seat mod is definitely required but luckily there are several mods to choose from. I don't have it, but I think the Sportster seat looks killer on them.

After riding several different bikes, I would compare the Savage ride to a hopped up VW beetle. Lightweight, quick, no frills with an old-school mechanical kinda clunky-ness. Very agile and fun to drive, but not something I'd wanna take on a long trip. Sure, some people have done it but only the real troopers. Your old Honda was probably more like a... well, a honda car. A little smoother, more room, a little fancier... but definitely not a Cadillac. For $3-$4k, I'd personally buy a good used V-star. That's about the going price for them around here, but then again you don't leave any room for mods or additional comforts. The good thing about buying used is most of the common mods and additions have already been added. Same goes for the Savage only you'll get a lot of bike for about half the $$$, which goes a long way in my book! I completely understand the financial situation!

Or, drop 2 K on the Savage & have 2 K left for gas, tires, maintenance & a trip er 2..