Someone had a thread talking about "what would you do different if you had to do it all over again". There was a very solid quote where someone said they would have spent more and bought lighter mods (sometimes we go overboard on armor). Everyone has their opinion, and you are talking to mostly people who became mechanically inclined by force (Poverty, military, or a parent) and are happy about it. Since genetics have nothing to do with it, practice makes someone mechanically inclined and saves a lot of money. If you love your cruiser now, I have a feeling you will have an inappropriate love for it after working on it yourself.
You have a list of items. I would pick all the interior stuff and do that yourself. It will allow you to make it exactly the way you want, you can be creative. Remove all the seats, pull the carpet, clean it if there are no holes, it will likely look and smell new again. Put in sound deadening stuff, lots of threads on it(just search a little). Recovering the seats are not that complicated, but do take time if you are like me. I installed heaters too with new leather in the front. Really made it a lot nicer. Put in a new stereo and remove factory amp. You can get an amp/subwoofer for the back and there is a nice bracket you can buy from someone right on MUD or get the plans and make it. Doing it yourself will let you put in a much nicer system for less money, and you will appreciate it more.
While you are putting in speakers, you can put in new window channels so they go up and down fast and smooth like new.
Then touchup/polish up the paint and, maybe even polish the windshield. These things will get your feet wet and give you a good sense of satisfaction.
33" tires are just about perfect for light wheeling and overlanding, the ausies do hardcore stuff with them all the time.
As mentioned by others, you may be trying to really build it out too much for what you are going to use it for. (we all do it, so not judging)
Mine is light and the engine is plenty strong for what I want.
Not trying to discourage you from paying someone to do it, just saying that a lot of us enjoy both the building and the using. You might too. I wouldn't be afraid of it, too many people here can help you reverse what you do wrong.
300k doesn't mean anything other than a proven record.