$5.3M to use but 0 experience. Advice...?

[Alton P.]

Title says it all. Currently live in Orlando. Made money from other businesses in a relatively short time and at a relatively young age, and now want to put it into real estate. Problem is this would be my first real deal. I would like some general advice from the knowledged community about where might be best to deploy this (I did make an STR-specific post elsewhere, but this is for more general wealthbuilding advice). Also don't have any agent at the moment, insurance people, or loan officer (if I even get a loan), so open to advice from people here in their areas of expertise. I used to work in CRE acquisitions so I understand the numbers but lack deal experience.

Some stats: 

- I am open to both debt and all cash depending on circumstances. 

- My biggest parameters are long-term appreciation, and enough cash flow to comfortably live off of (which is why I'm strongly considering an all cash "park and profit" approach without worrying about crazy interest rates). I want to cash out at the age of 115 and use the cash to buy artificial organs to live forever, lol. Honestly that is the main goal and what both keeps me going and up at night, so I'd say the ultimate "end goal" is having lots of cash and the means to withdraw it down the line, WITHOUT going absolutely insane.

- To this end I have primarily considered Hawaii (Honolulu Oahu, Kihei Maui, and Kailua-Kona - either short term rentals or long term, ideally able to live in one unit/room of the property or properties), Miami, Houston, and Space Coast Florida. Hawaii or Miami would likely be an STR, Houston would be MTR, and Space Coast also a STR. I have a buddy in Houston with large lumbar and tool yard that I believe could make good prices for new development, but again, despite the cash, I am inexperienced and don't want to make a mistake biting off more than I can chew.

- While I can manage 1-3 STRs (I think, especially if I live in or near them) and one sub-15 unit multifamily complex, I definitely cannot for more than this on my own, and still have my other businesses to run, and want to leave adequate time to devote to those as they are my only revenue sources (another reason why I'm interested in some more livable cash flow).

- And i guess as a bonus, if you had this cash, what would you do to exponentially multiply it over a 100+ year period? I am considering buying self storage, branding it, turning it into a real business and scaling with more self storage facilities to sell to BlackRock in 2077 or something like that. Standardized, corporate, branded. Or maybe some adventurerous, extreme vacation rental business. Open to putting in the time and effort for that, but I have 0 experience with self storage, turning around some old mom and pop, or managing something like that outside of what I've read online. I am not a "handy" person. I don't want to lose this money on my first deal.

Overall, I'd love to live in Hawaii and collect 6-figures a year while living for free in one unit of a multifamily or multiple condo group, just as much as I like the idea of going all in on some big brand. I wonder, where is the balance, what would be best for now, and could I start with one and scale into the other as i grow experience and hopefully more capital? I know this is a lot, but I think it'd be an interesting discussion and would really appreciate some advice from the communtiy! Thanks.