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All Forum Posts by: Josh Green

Josh Green has started 21 posts and replied 354 times.

Post: Best approach to investing equity

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Kyle Badger:

Hello I am brand new to the experience of real estate investing and am looking for opinions on how to approach our first investment property purchase. We currently have a good amount available as cash equity in our primary residence. We are looking to invest this money in real estate and put it to work. Would the best approach be to find a cheaper home that would generate cashflow, and pay cash for it. Or is the better option to put it as a down payment on a more expensive home that would also generate cashflow. In both instances, the goal is to continue to use the equities of the homes we purchase to buy new real estate/investments. Greatly appreciate any and all opinions. 

Completely depends on the amount you’re playing with 👍. Shoot me a text and I’d be happy to call and go over options based on your situation

Post: House Hack Market Dilemma - Tampa

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Josh W.:

I’ve been looking for a house hack to rent by room in St. Pete/Tampa, but honestly the market has me unsure right now.

Seems like prices are dropping and I don’t want to catch a falling knife as they say. I'm a 23 year old first time home buyer, and I’ve definitely been stuck overthinking everything.

Is now a dumb time to buy? Or is waiting even riskier?

Would really appreciate any thoughts!


 Time in market > timing the market.  As a fellow house-hacker, I still remember being told prices were going to come down every year now since I bought my first house-hack back in 2019.  

In real estate and other investments, you lose when you sell low.  People sell low when they over leverage or are otherwise "forced" to sell.  The way you should think about it is this: You have to live somewhere. Rent has increased and followed pricing increases.  If you buy what you can afford and it pencils out today, you will be good in the long term.  If prices drop further, great!  Your property tax will go down too and your profitability remains the same.  If prices go up, great!  You are gaining equity now.

Another important aspect of investing is "dollar cost averaging".  I see too many people that try and time real estate act like they are only ever going to buy 1 piece of real estate.  If that's the case, that alone isn't much of an investment strategy - just like investing in a retirement account you need to continue to add to it and not hyperfixate on your one and only lump sum you deposit.  Dollar cost averaging is how you curb "risk".  Buy as frequently as possible.  Prices come down?   Great! You can get your next deal at a better price/profitability ratio than your first!  You didn't LOSE on your first deal, it is still profiting.

No offense, but the advice given above is terrible.  Buy when prices start to increase?  Prices increase when demand increases.  There is so much more cost than the purchase price in scenarios like this.  For example in recent years, when prices were increasing, they were going up so fast appraisals (which look backwards 6 months) were behind.  To be able to finance anything, you likely had an appraisal gap and had to come out of pocket in cash to cover it.  That is a much "worse" timing of a deal than anything.

The fundamentals of the Tampa Bay area are so strong long term.  The migration, the job growth, the desirability, etc.  There is no way that in 10-15 years or longer the prices of the homes here are not going to be at least double to triple their current values.  At a conservative appreciation rate of 4.5%, that leads to doubling in around 10 years.

I think a lot of people use the 2010-2020 range as a "baseline" which is a big assumption.  This was arguably one of the MOST affordable times in history to profit from, and invest in, real estate.  During that run, the average appreciation of real estate nationally was around 3-3.5% and more so for metros.  To assume we will see the same rates of appreciation over the next 10 years is absolutely silly - just take a look at any chart of the money printing in the US in the recent past (https://www.google.com/search?sca_esv=45b2a14af5ca2da4&r...).

This chart should blow your mind.  Assets like real estate tend to keep pace with and even exceed the rate of inflation.  We have not yet seen the full impacts of the money printing on inflation in the US especially long-term.  I would imagine that the inflation rate on average the next decade will be higher than the rate it was in the 2010-2020 range.  That will also directly impact housing appreciation.  Remember: it is less about the fact that houses are appreciating and more about the fact that your dollar is worth less and less (inflation).

Anyway, long rant.  I am an active investor, agent and house hacker.  I have helped many people just like you get into their first house-hack deal to set them up nicely for their 2nd, 3rd, 4th, etc.  There is more power for you as a buyer now, than there has been here in the past 5 years!  There is still opportunity to be had - and I definitely would not wait for interest rates to drop (my guess, they will come down to maybe 4.5%-5% in the late 2026 timeframe or early 2027).  When people can afford more due to rate drops, as we saw recently, that goes right into the purchase price.  Cars, houses, etc. When people can afford more suddenly, the owner of the assets get the advantage and will sell at a higher price because there is more demand.  

Post: Thinking of jumping into house-hacking for our first property

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Garrett Adams:

Hello all!

My wife, our infant son, and I semi-recently moved to the Tampa Bay area after I landed a great job in the area. I’m really enjoying the position, and my wife is loving the opportunity to stay home with our son for now while she prepares to go back to school to finish her nursing degree soon.

We've always talked about starting a rental portfolio focused on small multifamily, and it's a dream I've been especially driven to make real. I may have found a tri-plex that could be a great first step. We'd be going owner-occupied with an FHA loan at 3.5% down and likely use a 203(k) Limited to finance a new roof.

Once the roof is done, we’d re-tenant the property with market‑rate leases and move into one of the existing units. From there, I plan to DIY convert the ground-level garage under one of the existing units into a fourth legal dwelling. I'd pay cash for materials and do the majority of the work myself—keeping costs low. Once finished, we'd move into the new unit and rent out the one we were originally living in to complete the full 4‑unit plan, all within the FHA's 12-month occupancy requirement.

Some questions I’d love help with:

  1. Any investors familiar with South St. Pete, particularly the Harbordale / Childs Park area? What are your thoughts on tenant class, market rents for 1 and 2bd units, or code enforcement?

  2. Has anyone here successfully added a 4th unit through a garage conversion? Any tips on dealing with zoning, floodplain regs, or permitting in Pinellas County?

  3. For those who’ve used FHA + 203(k) Limited: any lessons learned or lender recommendations? I’ve read horror stories about lenders freezing draws or rejecting post-close changes—looking to avoid those pitfalls.

  4. General advice for first-time house hackers doing DIY improvements on a partially vacant property?

I’ve been doing a ton of research and modeling, and I feel this project could set us up for a strong start. Appreciate any wisdom from the community!

Thanks so much,
Garrett

Hey Garrett,

First off, I can’t express how important and excited I am for you to be committed to doing a house hack as your first investment.  I’ve personally house hacked multiple properties and used a variety of strategies from long term to short term renting and room by room.  This has set me up financially more than I could have comprehended.  It is a sacrifice, but a strategic one.

Ive helped dozens and dozens of buyers just like yourself find, and get into, a house hack here in the Tampa Bay Area.  There are so many ways you can do it here and there most difficult part of a house hack is simply that it is a more emotional purchase than any other investment.  You will be living there - your family will be too.  Balancing the comfortability to profitability index is key as you consider what to do; and understanding all the different strategies of house hacking is going to really open up the options you have.

I will somewhat second the mentions above: the 203k loan can be overglamourized on paper, and there’s a lot of assumptions you have going on in your plan that make me hesitate to greenlight it.  

if you’re not currently working with an experienced agent, I’d be happy to interview for the job.  I’m actually working two other house hackers at this moment with different strategies for each of them (both of them are single guys; one is looking for room/room and the other STR house hacking).  There’s a few properties I think you should consider based on what you’ve told me so far that I’d love to go over with ya.  

Post: Getting started with my first investment

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Alex Mcfarlane:

Hello, I am Alex. 
I am new to real estate investing but. I am in the Tampa area. I am currently looking for small  single family homes that will cash flow. 

I appreciate any advice on getting started. I would love to network with other likeminded people to assist with analyzing potential deals.

thanks in advance! 


Best bet is to get a value 4bd+ home and do room by room. OR, as a new investor, really a house-hack is a SOLID way to go. There's a few househacks on the market right now that would be a great start deal ranging from $400k-$600k. Some multifamily and some single family with an ADU. If your cash position is really strong though, you should be looking at STRs with me; those will bring you the most if you do them correctly.

Post: Tampa Real Estate Business Advisor

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Alec Strahl:

Looking for an experienced real estate business coach to coach me through my first deal over here in the Tampa area. What options would you recommend?


 As Ray mentioned above, hopefully you're working with a great agent to help coach you through something like that!  What strategy or deal are you looking at doing?

Post: Are there any Tampa Meet Ups?

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Darian Lupton:

Hey guys! I’m new to the Tampa area. Specifically Odessa, and I’m finally at a point where I can start looking to get serious about real estate investing. I’ve searched the forums and the most recent Tampa meet up post is 5 years ago. Also tried Meetup.com and can’t find any meet ups there either. I figure there’s gotta be something like that in this big city! Let me know if you guys know of any, thank you!

Feel free to DM me your number - I'll text you in a group with the two people that I personally know that run the biggest meet ups here in Tampa Bay

Post: Urgent: Need STR Market Advice to Slash Capital Gains Taxes – $250K Ready to Invest!

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Yair Zarmon:

Hi BP Community,

Newbie real estate investor here looking for some guidance from those with more experience.

I'm in a unique situation where I need to quickly purchase and manage a few short-term rentals (STRs). The reason? I sold a number of securities this year and must reduce my capital gains tax liability. To do this, I need to acquire STRs and prove material participation. That's not the hard part...the real challenge is choosing the right market on a short timeline without prior STR experience.

I’ve spent countless hours researching, underwriting, and convincing myself I’ve found the perfect market - only to second-guess and start over. I’d really appreciate any guidance or recommendations from those who have been through this process before.

Key details:

1. Out-of-state investing: I’m comfortable being a remote investor. With today’s automation tools, managing from a distance isn’t an issue.

2. Budget and financing: I have $250K set aside for this investment, and financing is essential to qualify for bonus depreciation and cost segregation - key strategies for offsetting my long-term capital gains.

3. Time sensitivity: I need to prove at least 500 hours of material participation before December 31, 2025, so time is of the essence.

If anyone has market recommendations or insights, I’d love to hear them! 

Hey Yair!

Pleasure chatting on the phone with you today 👍
I think we covered a ton of info that is super beneficial to you and would be to others.  

I want to add here for others that may be asking themselves if STRs are viable TODAY:
I operate in the Tampa Bay market - mostly Pinellas county (Clearwater, Largo, Seminole, St Pete, etc) and we’re making great returns with Todays rates, todays prices, and todays competition.
There’s three critical components to making this a success for myself and for my clients:
1) Buying the right properties at the right price points with the right locations and features
2) Budgeting for, and executing a professional finished product through a professional design and furnishing team with proven track record of success
3) Boutique property management to ensure your property is taken care of, continues to perform long term, and puts more money in your pocket by passing on the efficiency savings back to you (I charge 15% for clients only; at least at the time of this post)

biggest caveat:
You have to have an adequate cash position to make this work well. For clients who are out of state or otherwise wanting to be completely hands off, this means a cash budget minimum of $225k is recommended (20%-25% downpayment, closing costs, design and furnishing costs) and even better opportunities if you have more. Any less, and you are likely over leveraging, or not budgeting to create a great STR; which is how you fail as an STR investor. OR, you need to be very involved - 100-200 hours of time to self furnish/design/manage etc.

This can seem like a high barrier to entry for most newer investors, and it is, but that’s a part of why it’s lucrative. Much like running a business, you want to have the high barriers of entry - keeps the competition down and you more profitable 👍

If you or someone you know is ready per the above and wants to explore more the process and numbers, feel free to DM me and we can do an introductory consultation for free. I don’t like to blurt on here publicly the numbers or details as I’m also an active buyer (buying 2 more this year personally) and want to keep the business with those I trust and want to work with ✌️

Post: STR Viability in 2025 Onward

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Andre Lai:

Hello all,

New here and trying to learn different real estate strategies. I currently own a triplex that I am house-hacking. I've been looking into Airbnb for years but never pulled the trigger. What is the current viability of it now? Especially with the high likelihood that 100% bonus depreciation will be coming back. 

My team and I are buying STRs frequently - as long as you have the right people+knowledge in place it’s simply the most lucrative (that I can find anywhere) real estate investment strategy and ROI that doesn’t involve 7+ digits of cash. Taxes are due annually - rather invest to keep my taxes down and create passive cash flowing real estate with the appreciation upside!
I also operate in the Tampa Bay market - mostly Pinellas county (Clearwater, Largo, Seminole, St Pete, etc) and we’re making great returns with Todays rates, todays prices, and todays competition.
There’s three critical components to making this a success for myself and for my clients:
1) Buying the right properties at the right price points with the right locations and features
2) Budgeting for, and executing a professional finished product through a professional design and furnishing team with proven track record of success
3) Boutique property management to ensure your property is taken care of, continues to perform long term, and puts more money in your pocket by passing on the efficiency savings back to you (I charge 15% for clients only; at least at the time of this post)

biggest caveat:
You have to have an adequate cash position to make this work well. For clients who are out of state or otherwise wanting to be completely hands off, this means a cash budget minimum of $225k is recommended (20%-25% downpayment, closing costs, design and furnishing costs) and even better opportunities if you have more. Any less, and you are likely over leveraging, or not budgeting to create a great STR; which is how you fail as an STR investor. OR, you need to be very involved - 100-200 hours of time to self furnish/design/manage etc.

This can seem like a high barrier to entry for most newer investors, and it is, but that’s a part of why it’s lucrative. Much like running a business, you want to have the high barriers of entry - keeps the competition down and you more profitable 👍

If you or someone you know is ready per the above and wants to explore more the process and numbers, feel free to DM me and we can do an introductory consultation for free. I don’t like to blurt on here publicly the numbers or details as I’m also an active buyer (buying 2 more this year personally) and want to keep the business with those I trust and want to work with ✌️

Post: Realtor in Bradenton FL with AirBNB investment experience

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Raymond J. Rodrigues:

@Josh Green is this in your neck of the woods or can you refer them to anyone that you know? 

Yeah I cover Bradenton ✌️@crystal DM me and we can jump on an intro call next week to discuss 👍

Post: STR/Vacation property financing

Josh Green
Posted
  • Realtor
  • Tampa/St Pete/Clearwater, FL
  • Posts 377
  • Votes 341
Quote from @Dustin Pavlik:

Hello,

I'm an investor located in NWPA. I currently own 50 LTR units in my local area. I am interested in getting a STR in the St. Pete area, which would also be a vacation property for my family. I need some help finding an investor friendly lender in the area who could help me through the process. Also, a realtor who is familiar with dealing with STR investors and the specific area would be helpful. Thanks in advance!

Hey Dustin!

As an agent I've helped at least 50 people buy a successful STR the past 2 years - so all with todays prices, todays competition and todays rates. I've also bought 3 myself the past 18 months. I have all 3 phases for clients out of state: helping you locate and buy the correct buy box for success, a world class designer and furnishing team to create a top listing, and I also co-host property for clients at a discounted rate to ensure you're getting as much cash flow as possible. Feel free to DM me if you'd like to do a consult call and we can see how we can help and if it'd be a good fit 👍

@Raymond J. Rodrigues is an excellent STR lending broker I’ve done a lot of deals with so definitely reach out to him for that!