What to do? FIRE, Multi-Family Landlord, Hawai'i with rental on property

[rolliefingers]

I would like a few opinions from this esteemed community on our options.

Six months ago, we shrugged off our Midwestern McMansion & cut our costs.  Drastically.  Our stache is over $2.5mm invested and, now, our expenses are at about $70k.

Plainly we can FIRE now, yet we march on in our day jobs like dutiful employees for the time being. 

In lieu of having a typical day job, I am intrigued by becoming a multi-family rental (i.e. apartment building) owner.  I am educating myself on the subject and I believe it is something I can handle for sure.  Is this foolish or just plain greedy? 

If we were to indulge and do exactly as we wish, we would move to the Big Island of Hawai'i (not the side with the volcano) and have a rental unit on property to defray what would be a healthy mortgage.  We have been approved for $1.4mm but would likely not use even half of that if we go this direction.  Midwestern winters are the worst and we would not miss them for even a minute.

Thanks for any input.

[effigy98]

I have researched this for many years and we go to Hawaii yearly and do plan on moving there eventually. I have been told to rent there for at least a year before you make any decisions as many people end up making a huge dent in the nest egg because they changed their minds and found island living was not right for them.

[goosefraba1]

Dibs... Tropic life sounds outstanding right now.

Have you thought about Costa Rica or Panama?

Both are a 5 hour flight instead of 12+ (from Ohio). Both are much more affordable. American dollar goes much farther.

I agree... try before you buy.

[Johnny Aloha]

In lieu of having a typical day job, I am intrigued by becoming a multi-family rental (i.e. apartment building) owner.  I am educating myself on the subject and I believe it is something I can handle for sure.  Is this foolish or just plain greedy?

Neither.  Education is key.  Luckily for you, there is no shortage of free podcasts to figure out how to make the transition.  I strongly encourage this if you think you'll enjoy it - I do.  But be cautious of where we are in the market cycle, and never put too much faith in a broker's pro forma. 

If we were to indulge and do exactly as we wish, we would move to the Big Island of Hawai'i (not the side with the volcano) and have a rental unit on property to defray what would be a healthy mortgage.  We have been approved for $1.4mm but would likely not use even half of that if we go this direction.  Midwestern winters are the worst and we would not miss them for even a minute.

I'd rent for a year on the big island because the market is less liquid - in other words, most of the decent jobs are on Oahu so it might take you a while to sell.  Big Island life is different from Oahu life, so you might want to try out both before making a long term decision.  But Hawaii is amazing, enjoy your journey!

[rolliefingers]

I have researched this for many years and we go to Hawaii yearly and do plan on moving there eventually. I have been told to rent there for at least a year before you make any decisions as many people end up making a huge dent in the nest egg because they changed their minds and found island living was not right for them.

Aye - I have heard this sentiment over & over.  Noted.

[rolliefingers]

Dibs... Tropic life sounds outstanding right now.

Have you thought about Costa Rica or Panama?

Both are a 5 hour flight instead of 12+ (from Ohio). Both are much more affordable. American dollar goes much farther.

I agree... try before you buy.

I just spent 10 days in Costa Rica in search of the Aloha Spirit -- it isn't there.  Apples and Oranges.  United States versus the third world, albeit a beautiful land and people in its own right.

[rolliefingers]

Thanks Johnny -- is there a rural section of Oahu you would recommend?  We are planning a trip in Feb and are open to exploration.  Maui is amazing and has the price tag to prove it.  Kauai is too quiet for us.  BI is awesome but does have limitations as you point out.  If Oahu has some middle ground then I am open to your counsel.  Mahalo.

In lieu of having a typical day job, I am intrigued by becoming a multi-family rental (i.e. apartment building) owner.  I am educating myself on the subject and I believe it is something I can handle for sure.  Is this foolish or just plain greedy?

Neither.  Education is key.  Luckily for you, there is no shortage of free podcasts to figure out how to make the transition.  I strongly encourage this if you think you'll enjoy it - I do.  But be cautious of where we are in the market cycle, and never put too much faith in a broker's pro forma. 

If we were to indulge and do exactly as we wish, we would move to the Big Island of Hawai'i (not the side with the volcano) and have a rental unit on property to defray what would be a healthy mortgage.  We have been approved for $1.4mm but would likely not use even half of that if we go this direction.  Midwestern winters are the worst and we would not miss them for even a minute.

I'd rent for a year on the big island because the market is less liquid - in other words, most of the decent jobs are on Oahu so it might take you a while to sell.  Big Island life is different from Oahu life, so you might want to try out both before making a long term decision.  But Hawaii is amazing, enjoy your journey!

[goosefraba1]

Dibs... Tropic life sounds outstanding right now.

Have you thought about Costa Rica or Panama?

Both are a 5 hour flight instead of 12+ (from Ohio). Both are much more affordable. American dollar goes much farther.

I agree... try before you buy.

I just spent 10 days in Costa Rica in search of the Aloha Spirit -- it isn't there.  Apples and Oranges.  United States versus the third world, albeit a beautiful land and people in its own right.

Fair enough... I prefer the Pura Vide over Aloha, although we have only been to Kauai :) Can't go wrong either way. Hawaii does have the definite advantage of stability and US healthcare over Central America.

-Side note, Guanacoste region is my favorite area that I've been to in CR.
-Side side note, my wife and I won a 7 night trip with 3 rooms to northern Panama mountains for next year. I'm excited to check it out as well.