Myth 1: STRs create huge tax lossesActually, healthy STRs are supposed to be cash cows.

Final ThoughtsHilton Head’s condo market isn’t “booming” — it’s stabilizing, and that’s healthy.

Huge red flag I own seven properties. 40 Grand would be a healthy down payment for myself.

To date, our combined projects have yielded 320 preliminary plat approved lots across 101 total acres in three different counties and have generated a nice healthy return. 

2) You mentioned costs other than mortgage being out of pocket - what are your reserves and how long will they cover the costs you project with a healthy contingency?

Not to disqualify myself, but if I can get a good review on the difficulties of this program, then I might feel safer to purchase it, not thinking that it's just being sold as this all perfect program.That being said, I'm hopeful to get involved with these people and the community and mentorship they offer, and hope to find someone who has a not so good experience so that I can get a healthy review of what is to come.

Then, the conversation goes sideways when you tell them you are an investor and what you are trying to do.The reality is most Realtors are not investors themselves and do not speak investor lingo or understand what you are trying to do.The key is to find an investor friendly Realtor with a teacher's heart in the area you wish to invest.A healthy percentage of my clients are investors from around the country.Those Realtors are out there and happy to help.To Your Success!

PetePros:You lock in your own housing cost and start building equity.If your job situation changes, you could convert it to a rental later.Florida still has solid long-term appreciation potential.Cons:With your budget, you’ll likely get limited cash flow - and might even go negative after taxes, insurance, and maintenance.If you move, managing or selling could get tricky.This route makes sense if you’re certain you want to stay in the area long-term or you find a home that could double as a strong rental later.Option 2: Keep renting and invest out of stateThis is the path many people take when local markets don’t make financial sense.With $100K, you could easily get into a few cash-flowing rentals in affordable markets - like Memphis, TN, where I’m based.Here, homes in solid working-class neighborhoods still trade in the $100K–$150K range, and rents often fall between $1,100–$1,400/month, leaving healthy margins even after property management and expenses.If your goal is to start building a rental portfolio, investing out of state now might actually accelerate your path to financial freedom more than locking all your money into an expensive primary home. 

A healthy 50 year today is expected to live to 90.

My first choice owns healthy investments and helps me follow suit.