Newbie diving in with a house hack / STR!

Tampa, Florida
New Member Introductions
10moFollow

Newbie diving in with a house hack / STR!

Cassandra M StantonPro Member
Saint Petersburg, FL · Member since 2025 · 9 posts · 9 votes

Hello all! Not COMPLETELY new to REI - but new to the Bigger Pockets life.

I've had a LTR in Virginia for about 5 years and am getting into house hacking + STRs for the first time. I LOVE my neighborhood of St. Pete and am scheduled to close on my 2nd property in about a week!! I'm so nervous and excited. Looking to buy another multi-family in the next year or so (doesn't have to be a STR).

I'm an active duty Marine Officer with about 2 years left before I can retire, so I absolutely want to maximize my W2s while I can.  I also want to take advantage of all the veteran's assistance programs out there.  Ideally I'd like to stop HAVING to work in about 10 years and just live off of my REIs...

Looking forward to connecting with other like-minded investors and hopefully find a mentor or two...I'd really love to expand into other markets (I love Tampa, but it ain't the cheapest)!

Looking forward to meeting future friends on here!

3Reply
116 views

Most Popular Reply

Amber Stout
Lender · Tampa/Saint Petersburg, FL · Member since 2014 · 356 posts · 148 votes
10mo

Welcome Cassandra. I'm in St.Pete as well - we have the BEST community. I started out house hacking too (still do) and now I’m a mortgage broker helping others create financial freedom through real estate here in Tampa/St. Pete.

If you’re planning another multi next year, definitely use that W2 while you’ve got it — HUGE advantage before you retire out of the Marine Corps. Also, thank you for your service. 

There's some great meetups in the area, happy to share those with you if you're interested! 

Congrats on closing your second property — that’s a big deal. Excited to see where you take things. 

1Reply
See this reply in the discussion

7 Replies

Jump to latestLatest
  • Denver McClurePro Member
    Financial Advisor · Flower Mound, TX · Member since 2018 · 659 posts · 479 votes
    10mo

    Semper Fi @Cassandra M Stanton and happy birthday! I'll be out celebrating tonight with a few of my fellow Marines! 

    Feel free to PM me if you'd like to bounce ideas around. I've house hacked several times, own STRs, MTRs, and LTRs so I have a fair bit of experience (good and bad). 

    [email protected]
    1Reply
  • Amber Stout
    Lender · Tampa/Saint Petersburg, FL · Member since 2014 · 356 posts · 148 votes
    10mo

    Welcome Cassandra. I'm in St.Pete as well - we have the BEST community. I started out house hacking too (still do) and now I’m a mortgage broker helping others create financial freedom through real estate here in Tampa/St. Pete.

    If you’re planning another multi next year, definitely use that W2 while you’ve got it — HUGE advantage before you retire out of the Marine Corps. Also, thank you for your service. 

    There's some great meetups in the area, happy to share those with you if you're interested! 

    Congrats on closing your second property — that’s a big deal. Excited to see where you take things. 

    1Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    10mo

    Congratulations on the new property. St. Pete is an amazing market and you are setting yourself up really well. I’m in Sarasota, so not too far from you.

    From a tax angle, being active duty actually gives you a few big advantages right now. You can use VA loans to stack house hacks with very little money down. Since you've been house hacking, you probably already know about depreciation on the rental portion, allocating expenses, and potentially qualifying for the home sale exclusion if you live there long enough.

    With your new STR properties, keep the STR loophole in mind: if you materially participate (make sure you start tracking your hours now) and average stays are under 7 days, your STR losses could offset active W-2 income, which can be huge while you’re still in the military. There are also some other military-specific tax strategies out there you might consider.

    Thanks for your service, good luck, and happy to connect!

    [email protected]941-914-7779
    INVESTOR FRIENDLY CPA®5241 Reviews
    WebsiteView Page
    TaxMD® | AI-Powered Tax Planning
    WebsiteView Page
    0Reply
  • Samuel Awosolu
    Lender · Florida / Georgia · Member since 2025 · 58 posts · 28 votes
    10mo

    Hello @Cassandra M Stanton

    Congrats on closing on your 2nd property! I'm very familiar with the St. Pete area. Actually have an investor client selling a rental property in Clearwater that is newly renovated 10 mins from the beach.

    You should consider looking up north towards New Port Richey and Palm Harbor. If you self manage your properties, those areas would be great locations to acquire rentals. Values are still very reasonable and you can investigate doing MTRs for corporate housing or for healthcare professionals.

    Feel free to reach out if you need cost analysis on deals you are looking at or if you want to brain storm what if scenarios with some of the properties you are seeing out there.

    1Reply
  • Elealeh Fulmaran
    Specialist · Member since 2025 · 483 posts · 270 votes
    10mo

    Congrats on the new St. Pete buy and thank you for your service. With two years left, I'd run a simple two-track plan: maximize VA benefits for house hackable small multis now, and build an investor pipeline for your next buy. Lock a buy box near bases/hospitals for STR/MTR potential, get preapproved with a VA-savvy lender, and confirm rents with two PMs. On the ops side, analyze 10 deals a week, make 2–3 offers, and post a weekly progress update to attract mentors. Use meetups to build your core four and ask for intros to owners doing your exact strategy. One action this week: verify regulations and rent comps on five properties within your box and line up your lender call.

    1Reply
  • Cassandra M StantonPro Member
    OP
    Saint Petersburg, FL · Member since 2025 · 9 posts · 9 votes
    9mo

    Thanks @Amber Stout !  I would LOVE to meet some like-minded investors at local MeetUps.  Yes, please send them my way.  I'm so excited to really dive into this journey and want to learn as much as possible!

    0Reply
  • Cassandra M StantonPro Member
    OP
    Saint Petersburg, FL · Member since 2025 · 9 posts · 9 votes
    9mo

    Thank you @Ashish Acharya - I appreciate you assuming that I already know about all these things lol. I have been reading/learning about the STR loophole, but I am unfamiliar with a few of the other things you mentioned. I am tracking my expenses/hours and keeping a detailed record of everything. But come tax time, I'm absolutely going to work with a professional so I don't miss anythng!

    0Reply
Join the conversationCreate a free account to reply, vote on answers and follow this thread.
Log InJoin for Free