What Would You Do if You were Me?

Question

• Single, 41, no anchors. Debt-free with perfect credit. Never owned a home. Have no "dream" location, traveled lots and haven't found a place I wanted to stay yet, I like to move, I love change.

• 10 years in rentals, 7 years in estate management, 4 years flipping raw land.

• At my current job (Las Vegas) for 7 years, but actively applying to jobs. New job will be anywhere in U.S. (or if I'm lucky, internationally) and will last 3-5 years before packing up and finding a new location to work.

• My ultimate, 'someday' dream is to own vacation rentals in a tropical location where there's good diving (most likely not in the US).
Something with 10-20 units that I can live on and eventually move a couple close family members to as we age. (Just to give you an idea of where my head's at)

Some questions I struggle with:- Where should I invest?  I think it is probably best for me to pick a successful rental market and just build my base there (buy and hold forever), regardless of how I personally feel about the area.  The other options would be to buy as much as I can while in a certain area, moving onto the next and doing the same.

- Should I wait until I find the next job in hopes that it is in a great market and then I can begin locally?
I love the idea of managing my own properties (or at the very least, being nearby), given that I know how to do it and am good at it (and I am a control freak and hate entrusting my livelihood to others), but I know that I don't want to live in the same area for 20 years just so I can be close to my properties (even if that property is in Fiji and I own a dive business - I know after a year or two I'd be bored of the dive sites, bored of the food, bored of the views...)
I also feel like it would be a shame to waste the 7 years at this job when it comes to financing - but the clock is ticking on that and I have yet to decide on an area to invest.

Of course I have a zillion other questions rattling around in my brain, but I'm going to open it up to you, the brilliant hive mind of BP!

What would you do if you were me?

Anything goes! I'm open to to all criticism too (oof, scary thing to say on the internet LOL); what should I know, or think more about?
Any advise or suggestions are greatly appreciated - I'm a sponge!!
Thanks, everyone!

Account Closed · Answer

I think the ultimate point of investments is to give you the freedom to live wherever you want and do whatever you want.  I would never want my investments to determine where I live. So invest wherever you want that will give you the income to live anywhere.

Antonio Cucciniello · Answer

Hey @Sara Ant!

So if you want to own vacation rentals and that is going to be your strategy, then I would pick a market that allows for that.

Start first with your goals. If you want to own 10 to 20 units, what do you want those units to do for you? Allow you to travel the world? Then you will likely need them to produce cash flow.

From there, what is your strategy? If its consistent cash flow, you might want a long term rental option versus short term rentals, but thats just me

Then pick a market that allows you to do that strategy, and base it off data points. Once you have that, go there, look for properties, analyze them and build your team while you are there and then when you are bored of it, you have the team in place, and manage it remotely, visiting every once in a while when you get bored of the place you are at..

Side note, hearing about how much you seem to like change, its odd you stayed at a current job for 7 years. I hate change and have had 3 different jobs in 5 years

Jessica Brennan · Answer

@Sara Ant I think it matters some how much you have to invest, you are going to be able to purchase more houses faster in the Midwest if you have 50K thank in Cali. I currently invest in the midwest market and am really loving it. it isn't were I see myself living forever, but my business is doing much better than I dreamed and I can see myself investing here for a long while.
I also wouldn't wait, the rates are so great right now that if your planning on holding for awhile you can't beat the 'free' money that the banks are handing out.

If you have any questions about the midwest markets I'm more than willing to help! Good luck!

Lynnette E. · Answer

Hawaii, go there and buy something you like.

Drew Sygit · Answer

Find markets where you can find workers you can trust.

Have heard horror stories about foreign countries eating investors alive.

If you want to hang out for 3 years and then move on, you'll need to hire a trusty crew while you're there, so they can run when you move.

Sara Ant · Answer

Thank you for your responses! I sure have some thinking to do...I have about $30k cash, I think my best bet is to purchase while employed otherwise I may be denied until I've built up enough time at a new job (which who knows, maybe I'll just take 6-12 months to travel for a bit before the next job...)The hardest part of my decision is whether I want to do this at all... so much time in property management has taught me that tenants are crazy (I should have been writing a book!) - for example, a state employee who wears a suit everyday and makes 6 figures, smears feces all over his bathroom walls and the tub has a line of what seems to be a feces water ring...I have had a lot of success in land flipping and the freedom of that has spoiled me (no tenants, toilets, or inspections, just cash in my account every month).  I paused that because I don't enjoy the market research and selling side of it, but when I dig deep, I realize rentals are not going to be any more enjoyable in those aspects (trade selling with renting/managing), and would be even more hassle in general.

Then I see a 3B, 2B on an acre of beach in Fiji for $300k and THAT moves me.  I know I need a powerful 'why', something to get me out of bed and investing every day - I think when I dig deep, rentals just aren't doing it for me...

I've never been one to do it like everyone else, and I'm thinking maybe this is no different, maybe I need to think outside the box in this aspect as well and come up with what fits me and lights my fire... (For example, I quit my job and got rid of everything I owned to travel full-time, even though I was broker than a joke.  I spent 11 months traveling, landed a job on a beautiful horse ranch as a dog nanny where I make more than I've made in all of my years working, all living expenses paid plus crazy perks and bonuses, and I work maybe an hour a day - that's the type of life I strive to build for myself, the "impossible".  The more I think about buying up a bunch of houses in MO and managing a PM firm from the other side of the country, I just don't know...)

I appreciate all your responses, they certainly help me weed through this huge life decision!!

Karl B. · Answer

-"Should I wait until I find the next job in hopes that it is in a great market and then I can begin locally?"

I'd do this. Hopefully you'll move somewhere with some cash flow potential. If not, you can always invest elsewhere, but I'd personally hold off until you know where you're going to be living so in the event you move to Cashflowville you will be able to begin buying once you're ready.

Julio Garcia · Answer

Sounds like you should invest in FL, while its cheaper than other coastal places.

Also, theres tons of rental/vacation opportunity in HI, my friend is over there making a killing on it

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