Tampa, Fort Myers, or HAWAII??

8 Replies

Hi Bigger Pockets,

My family and I are considering moving to one of these 3 areas:

->Tampa/St. Petersburg, Florida

->Fort Myers/Cape Coral/Naples, Florida

->Oahu (Honolulu), Maui, or the western side of the Big Island (Kailua-Kona) in Hawaii

With that said, here are our MAIN considerations:

#1: Warm water and warm weather

Everyone in our family loves the water and why we've narrowed our search to these 3 areas


#2. Schools
On top of having good public schools for our kids to attend, my wife used to be a teacher and is currently an assistant principle, so a state/municipality that values our educators in terms of how they treat and compensate them is also important for us

Both the Tampa and Fort Myers areas are relatively affordable, Hawaii ...yeah, not so much, but I believe we can overcome that obstacle (more on that below). Basically

#3. We MUST house-hack
A.) FHA & Multi-Family Units:
4-unit multi-family is preferred, but not necessarily required, especially given how difficult they are to come by in some markets. I forget off the top of my head if it's a one-year, or two-year commitment to owner-occupy the property if you use an FHA loan(which we fully intend on doing to take advantage the 3.5% down requirement). Upon fulfilling the length of time required by the FHA for owner-occupants, we move out and really reap the rewards from a cash flow perspective, and either repeat the process entirely and buy another multi-family, or purchase and move into a single-family home (that's a "good" problem for us to save later on!)

**We're a little confused though on the loan limitations the FHA has. Here's why:


The stated FHA max limits are dependent on location, I get that, BUT, for example, the basic standard mortgage limits for FHA insured multi-families in Honolulu are as follows:

2-Unit: $923,050

3-Unit: $1,115,800

4-Unit: $1,386,650

HOWEVER, even though the max limits as shown on HUD's website for Honolulu show those that I've typed above, on the same page, if you scroll down a little bit, they go on to state, "Section 214 of the National Housing Act provides that mortgage limits for Alaska, Guam, Hawaii, and Virgin Islands may be adjusted up to 150 percent of the new ceilings."

So, if I follow this correctly, if we were to move to Honolulu and purchase a multi-family, we could actually borrow a max of $1,470,475 for a 2-unit, a max of $1,777,375 for a 3-unit, and a max of $2,208,825 for a 4-unit ...is this correct???

B.) Real Estate Investment Potential: 

Ideally, we'd like to AirBnB out the other units as we live in the other as we *should* get a better return than if we were to rent them out to a tenant. In the 3 markets were considering moving to, we'd expect some seasonal fluctuations in demand/pricing elasticity, but overall, would expect to have some relatively healthy occupancy rates year-round (say, 70-80%)

Appreciation would be more the icing-on-the-cake than anything, so a properties ability to CASH FLOW is more important to us than the rate with which it may appreciate in value. In terms of monthly expenses, we'd LOVE to get close to breaking even ...when we're living in one of the units and cash flow isn't an expectation of ours ...while we're living in one of the properties units

We're desperate to pack up and move to one of these areas tomorrow!! If you'd be willing to share any advice, thoughts, concerns, or which market you'd pick and why, WE'D LOVE to hear it and be forever in your debt!!!

Thanks for reading!

-The Rittmann Family

@Nick Rittmann

My family and I are moving as well this summer and we picked Maui, Hawaii. I started purchasing short term rentals, house and a land that I’m developing for food truck park. That being said, I’ve done my research in the area. My son is going to a charter school in Kihei which is a technology school and that’s what we prefer. There’s a really good school in Makawao but that’s upcountry.

With your investing, being in Maui look into USDA loan since majority of land in Hawaii is considered “rural” you’ll be able to get a loan with zero downpayment and this has to be your primary residence. You can find property that has Ohana which is a guest house and use that as a rental. I’ve purchase a house in Kihei that has 4 doors (main house 3bed/2 bath and 3 door with 1 bed/bath) it was listed as a house and when I visited the property i unraveled that there’s plenty of room to make an income, so keep an eye on those. Airbnb/VRBO or any sort of short term rental in Hawaii, one of the rule is that you have to own the property for 5 years before you can apply for a permit so be careful relying on short term rental and research it.

I hope this helps a bit narrowing your decision making. Goodluck!

@Janice V.

That's some awesome info, thank you for sharing, Janice! For whatever reason, we never considered using a USDA loan because we never thought of Maui or the area around Kona on the Big Island to be "rural", but hey, it's not our definition of the word that matters, but the governments! That's a GREAT idea

We've also noticed that a LOT of properties listed in Hawaii are listed as "single-family" when in fact, they have, as you mentioned, an Ohana, and/or, say, a unit above the garage, a studio on the ground floor, etc. and you would think, be listed as a "multi-unit"? 

If you don't mind my asking, what were some of the reasons you chose Maui over Oahu or the Big Island??

@Nick Rittmann

I personally don’t know why they don’t list it as multi heck they don’t even seem to list it in major sites. I’ve drove around and notice majority of homes are not listed in Zillow. I found Keller Williams agent app able to pull all the listing from all the local broker.

So, I’m from Oahu and left the island when I was in my 20’s to travel and live around the world, I felt at that time I was having island fever. Lived overseas for almost a decade I then settled in Las Vegas almost 10 years ago when I got into real estate investing. Visited Maui summer of 2018 for my son’s birthday and felt time to come back home and raise my son there. Warm weather, warm people and most of all.. there’s a lot of opportunity when it comes to business and real estate (which another story) hahah I cant share too much or else everyone will move to Hawaii! JK

I’ll share more just shoot me a message

@Nick Rittmann I am a Realtor in the Fort Myers area, so I will do my best to answer all of your questions!

1.) Obviously you already know our beaches are great with very warm water here, with places like Sanibel Island and many other popular beaches just a short drive away, you definitely picked a great spot if that's an important factor.

2.) We have a great local school system here with plenty of options ranging from public to private and charter schools as well. Florida as a whole is also making big strides forward in leading the nation on education reform with recent salary floors for teachers established and new curriculum guides in the works. Our new governor is the one who has established these new principles and he has a high interest in the matter so I can only see it getting better from here.

3.) (A.) Just to clarify, the FHA guidelines state that the unit must be owner-occupied for 1 year, as your primary residence. As you stated, three and four unit properties are fairly hard to come by in this area, but they are still out there occasionally. Duplexes, however, can be found throughout all local markets at a huge variance in price level and offered amenities to fit your needs.

3.) (B.) As stated previously, the supply of available duplexes that we have in the area lend to a great rental market. Although our beaches are great here and lead to a strong summer rental season, the stronger rental season is over the winter because of the snowbird population that we see here. The season ranges roughly from October-March and throughout this time, you can expect a very low vacancy rate in any desirable area nearby. Good renters will also continue to come back year after year, so this is a great way to build a reliable base for 4-6 months of the year. With the other 6-8 months of the year, you certainly have options in renting the available units. Some units are listed with only year long lease contracts, and although they do still find buyers most of the time, this is one of the more difficult options to find a buyer for. This isn't uncommon in the area though so it is certainly something you could mention to your winter renters. Your second option would be finding a tenant to hopefully sign a lease for the entire period that your unit is not occupied. This shouldn't be too difficult as we have a fairly strong rental market at the moment. Your third option, being AirBNB or any other short term rental outlet, would be the most work, but would certainly work great to fill in any gaps you have left over after. That's not to say that this couldn't still be your primary method of rentals though, it would completely depend on the amount of work that you're willing to put in. 

Hope this helps, PM if you have any questions at all or if you're interested in looking into any specific properties to get a general idea of what the area has to offer!

Hi Nick,

I can't claim to have many answers for you but I can bring up some details that may be important factors to include in your deliberations. I'm a small time investor in Minneapolis (triplex), with a long-term SFH rental in south Kona I hope to early-retire to, and my folks have been living in Naples, FL since the mid-90s where they've funded their early retirement with long-term rentals of condos. You are smart to consider all this as a choice of your own home, with potential to off-set your personal living expenses with rental income.

#1: Warm water and warm weather


It all comes down to personal preference but to me, as an avid snorkeler and SCUBA diver, there is no comparison between Hawai'i and
these locations in FL. Some parts of the FL Keys would compare. Have you spent time in all these places and feel like you have a sense of the local culture? Are you going to regret moving very far away from friends and family to HI? Life on an island, especially one as small as Maui or as small population as Hawai'i is very different in subtle ways that you might not notice while on vacation. Many Hawaiians don't bother making friends with newcomers because it is so common they can't hack it and go broke or get too home sick and return to the mainland within a year.

Remember to factor in that with warm weather and warm water also come risks of storms, flooding and hurricanes. FL has taken a real beating in the last few years and looks like it will continue as the climate warms. With some elevation on west Maui and west Hawai'i it more rarely has these issues but do have a history too. Look at insurance rates, and the uncertainty of future insurance costs and factor it in.

#2. Schools

I don't have kids or work in Ed so don't know much about this but can tell you I see a lot of educators in HI complain in the neighborhood FB groups etc. about low wages compared to the cost of living. COL in HI is a huge issue in general. Food, utilities, gasoline and housing are all extremely expensive. There are online calculators to show you the comparative COL. Be prepared that you may need to make major lifestyle changes in order to make HI affordable. Buying is similar cost to southern CA though I feel there are better deals and less competition to be had for places needing remodeling. Try to reach out through professional and neighborhood groups and get a real sense of what pay vs. COL in HI is like.

#3. We MUST house-hack

There are lots of investment properties that meet the 1% rule to be found in FL. But they may not be MFH or a place you want to live with your family but finding cash flowing properties should not be a huge challenge. HI meanwhile is much more expensive to buy and local incomes can't generally support reaching the 1% rule. Vacation rental will get you much closer though but there it gets sticky with local regulations/neighborhood covenants, changing regulations and tying your priorities for a personal residence together with properties that are good performing vacation rentals. The prevalence of "ohana" units in HI opens up lots of flexible options though. I wouldn't want to buy a place if I MUST have the higher cash flow as a vacation rental or it would be unaffordable.

Things I learned are important to know when buying in HI:
1. types of utilities (solar? -- is it leased or owned, just for hot water, is there whole-house battery back-up?; is the water city or catchment?; Is the sewer city or cesspool or septic?; anything on propane?)
2. leasehold vs. fee simple ownership
3. is internet and cell service available and reliable?
4. is the area dependent on a single transportation route in and out (likely to get stranded when there is an accident on the main road)?
5. What lava zone is the property in and can I get HO insurance?
6. What are the local laws and neighborhood covenants on long and short term rentals? Are they considering changing them?
7. Dealing with stuff we don't have in MN - vog, termites and earthquakes


I can also recommend the podcast called Afford Anything. 50% of the episodes are answering listener questions and 50% of those are dedicated to REI. The host often walks through ways to think about options like this and how to wisely separate investment decisions from personal lifestyle decisions.

I hope this is useful to you. Feel free to message me if you want chat!




@Nick Rittmann Following up on the string of messages with @Janice V. Two things to clarify: 1) USDA loans apply only to properties located in specific rural areas so check with USDA and/or a lender familiar with USDA loans; 2) In our MLS, residential properties are identified as single family, single family with attached ohana or single family with detached ohana. You are experiencing what many home shoppers experience when using third party sites - the inability to parse out the various home types.

If you are looking for a multi-family/dwelling property to Airbnb, look carefully. The laws in Hawaii are changing as it pertains to residential properties. For the most part, condos have so far been left alone (sounds like that is not what you want anyway). On Maui, there is a five year waiting period from the time you close before you can apply for a permit to legally rent out short term on Airbnb (again, residential properties only). The "loophole" is to find a multi-dwelling property where you live full time. Apply for a B&B permit (still have to go through the permitting process because they are not transferable) but right now there is no waiting period. And, there are some good properties available if you need some help.

Janice also mentioned schools. Kihei Charter is a good school if you can get in but I've heard that there is a wait list. My son attends Seabury Hall in Makawao. Great college prep school for 6 to 12 grade. There are also a lot of good elementary options.

Overall, Hawaii versus other areas? Look at year round tourism numbers. I think you'll find some areas drop off in the summer time. We don't.

Feel free to reach out if I can be of assistance!

I have been considering relocating to Naples, Florida also. From what I understand, you can't do Airbnbs in Naples. I'd welcome any comments from people who live in the area. You may want to strike that one off your list. I'd be very careful to investigate where you can and can't do Airbnbs prior to moving. Always have a contingency plan since laws are subject to change.

@Dana Kimberly You are correct, however, this ordinance does not apply to properties located in unincorporated Naples or any other city located in Collier county, unless otherwise stated by the HOA or other governing organization. However, Lee County just to the North (Fort Myers, Cape Coral, etc.) has no such restrictions.

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