The House:
You say the house cash flows $650/mo or $7800/year, and has equity of $175k. That's a yield of 7800/175000=4.45%, minus the costs of your labor and liability. An alternative to this investment might be an REIT fund like VNQ, which yields 4.64% at the moment. I'd probably go the REIT route because I'm lazy AF and don't like replacing roofs.
The Business:
That's a sweet gig you've got there, earning $50k for 6 months of labor in a relatively LCOL area! This semi-retired lifestyle could go on forever, except you suspect a lawsuit will eventually occur and wipe out the $75-100k you could have captured by selling it. You don't mention what assets are involved in running a party bus business - website, bus, and some "liquid assets" I suppose? Where I'm going with this is: If you are organized as an LLC and have adequate personal liability protection, and someone sues you and takes away your bus, business laptop, and margarita mixer, what's to stop you from starting a new company doing the same thing with all new assets? What's the replacement cost? How much of the replacement cost would insurance cover? That's what is truly at stake here. E.g. if the replacement cost is $80k, and insurance would net $50k, you could eliminate much of your business risk by just setting aside $30k in relatively safe, liquid investments.
The Investment Plan:
Let's say you need $30,000 per year in income. Your rent house or VNQ investment provides $7800 of that, so now we're down to $22,200. If you are using the 4% rule, you would need $555,000 to cover those $22,200. You have, let's say, $60k in stock already, plus another $60k in savings, so you need about another $435k.
At $20k/year in savings, this is going to take a while. The online calculators like networthify.com or similar will tell you how long. Obviously, you could work during the other 6 months and reduce your time to FIRE. Things start to get exciting quickly when you can save $50k/year. Set up a SEP IRA to reduce your taxes and learn about the backdoor Roth you can use to access those assets in early retirement.
100% in Disney? That's weird. I suggest diversifying by selling call options on the DIS stock until you are assigned (unless you are not willing to do many hours of homework first!). Then buy VTI.
