Should I start now or should I wait?

[Ryan H.]

Hi everyone,

Been a fan of BiggerPockets for a long time!

I’ve had an interest to invest in real estate for about 10 years now. 10 years back I was living in Portland, Oregon as a real estate agent.

Back then, I had enough to make a down payment on a property, but to make a long story short, I saw business opportunities in the Caribbean and used the money to open a retail business 9 years ago in the Caribbean.

Since then, I’ve opened another retail business in the Caribbean. Now after years have passed, and with 2 successful retail businesses, I’m looking to accomplish the goal I wanted 10 years ago.

I’m now 36 and I still live in the Caribbean, but I’m a US Citizen. I file my taxes in the Caribbean and the US, since I’m a dual citizen. I have a US bank account and I’ve been tracking my credit score, and it’s in excellent condition. I’m mainly interested in Portland Metro and surrounding areas, as well as Florida, mainly Broward County and surrounding areas. I’ve lived in both places, and I’m familiar with the areas.

My goal is to buy and hold for monthly cash flow, with the plan to buy a new property every year to two years. Because I live in the Caribbean, I wouldn’t want a place that needs much work, and is low maintenance. Almost turn key.

With my businesses in mind, I feel comfortable taking $20,000 from the businesses this year to invest. After many years in business, I have pretty accurate estimates of what I can invest each year. Currently, I project I’ll have $20,000-$40,000 each year to invest.

So does it make sense to invest $20,000 now? Can I realistically cash flow a property in the Portland Metro or Broward County with that downpayment? Or do I wait a year, when my investment amount should double? I’ve waited 10 years, and I’m willing to wait another year... but I want to make something happen now if it’s possible. You can’t accomplish your goals sitting on the sidelines.

Any advice or guidance from the group would be extremely helpful!

-Ryan