Seeking Advice on Investment Plans: Moving from Virginia to Florida

[Andrew Chase]

Hi everyone,

Please excuse my long post. I am planning my investing future and am hoping for some advice. I'm 28 years old and currently living in Richmond, VA. I bought my first house in 2022 and have had a roommate since then, who pays slightly more than half of the PITI. After making some updates, I now have $50,000-$70,000 in equity.

I'm moving to Florida soon and have decided to relocate to Jacksonville based on my market analysis and personal reasons. My plan is to rent a room for several months and buy a property in the winter to house hack.

I work remotely, so I'm looking for a low cost of living area. I have a 7% employer match and max out my Roth IRA. Even after these contributions, I still have a healthy amount of savings to purchase a second property, although it might take some time to save a 20% down payment.

My current plan is to rent out my house in Virginia, which should cash flow around $150/month after property management fees. I'm having the home reappraised and expect to drop the PMI, reducing the payment by $92/month(raising cashflow to ~$250/month). The property is in good shape, but will need a new HVAC system in the next 3-8 years, which could cost around $12,000.

Although I'll be out of town, I'll visit frequently so I will be able to check on the property.

Here's my plan:

• -Move to Florida over the summer.
• -Rent out my house and form an LLC in Virginia.
• -Before spring 2026, buy a property in Jacksonville with 3%-10% down and house hack.
• -Do a mild, cosmetic renovation using a combination of sweat equity and contractors.

Example of the type of house I'm looking at (currently under contract, just for reference):

1025 W Lawfin St, Jacksonville, FL 32211 | MLS# 2075886 | Redfin

Comparable for ARV:

1010 Arlingwood Ave, Jacksonville, FL 32211 | For Sale ($298,000) | MLS# 2080151 | Redfin

1126 Cathcart St, Jacksonville, FL 32211 | Redfin

    Another option I'm considering is purchasing a multi-family property. This would either mean living in a less desirable neighborhood or selling my current house to use the tax-free profit for a down payment on the multi-family property. This option would eliminate the headache of being an out-of-state owner and give me a fresh start in Jacksonville.

However, I have reservations:

1. -My current interest rate is 5.375%, which is lower than what I could get today.
2. -My house in Virginia is in a quickly developing area with many new businesses and a large county park opening in the neighborhood in fall 2025, which may attract more affluent families to the mostly blue-collar neighborhood

I don't feel ready to dive into a multi-family property yet and am not confident in finding a great deal on one since they are typically owned by investors. Although I believe I can find a single-family home at a good price, possibly even outside the MLS.

    Once I move into a house hack and can force some appreciation, I plan to save for another house to renovate and rent, or a multi-family property in a few years.

My long-term goal is to continue working my job, eventually transitioning my W2 into a consulting business while working as a real estate investor part-time, aiming for more free time and financial security.

What are your thoughts on these plans? Am I missing something important? Any advice would be greatly appreciated!

[Andrew Chase]

Quote from @Wale Lawal:

@Andrew Chase

You're on a great path—house hacking in Jacksonville while renting out your Richmond property is a solid strategy that balances growth with stability. Keeping your Virginia home could pay off long-term, especially with neighborhood development and your low interest rate, but if you're leaning toward multifamily in Florida, using your equity via a sale or HELOC could accelerate your portfolio. Since you're still early in your investing journey, sticking with a single-family house hack and gradually building confidence and capital before jumping into multifamily sounds both smart and sustainable—you're thinking like a long-term investor.

Good luck!

 Thanks Wale,

  I think I'll stay with single family for now, and perhaps sell the Virginia house in a few years to finance a multi family. 

I'm looking at the logistics of the move, and considering buying immediately in Florida instead of renting at first.  When I consider the costs of moving 2x, breaking a lease, etc it quickly adds up and I'm wondering if I would be better served buying a property at retail price.  There are many homes which have been on the market for 100+ days in the areas I'm looking at, and it wouldn't be too difficult to fly down to take a look and put in an offer.  

Obviously buying below market value is advantageous, but for a property to live in as well it has logistical difficulties.

I could stay in my current property until I have a house closed in Florida, then move down.  My employer offers me a lot of flexibility, so this wouldn't be too difficult.

Do you have any thoughts?