Be Honest.. What Challenges are you having in this business?

[Rob Gillespie]

I am writing this post more for the seasoned Investors.

It is very easy to see the results that everybody shows online, flying in private jets, not working, building hospitals in third world nations, but I want to hear the REALITY of what life is like for the seasoned investor out there!

I will begin by saying I am over 23 years in the business and full time form over 20 of that.

I work at it every day, there are always problems to solve from tenants, to banks, city inspectors, CONTRACTORS (LOL), etc...

I am blessed enough to have so many connections in my market that I can maintain deal flow of great off market properties with equity and not have to spend a ton on marketing. This allows me to offer great deals to my investment buyers around the world that like to invest in the Cleveland market. 

I never missed any of my kids events (unless I wanted to, LOL)

I have made a TON of connections which has opened up many business opportunities for me because of real estate. 

I am able to travel to Florida every month and still run my Cleveland Real Estate Operation. (I fly private on my big jet with 300 of my closest friends and allowed Spirit to wrap it for marketing purposes :-) )

My biggest challenge is that I believe Residential Real Estate can provide an amazing lifestyle, better than most surgeons, but it is not scalable enough alone to take me to the next level. 

My internal debate is should I move on from what I know so well after doing more than 1000 deals and start swinging for the fences on repurposing shopping malls or something, or stick to what I know and do well. (NOT LOOKING FOR AN ANSWER, JUST GIVING EXAMPLE OF MY OWN DILEMMAS AS A SEASONED INVESTOR)

Let's hear how REAL LIFE REAL ESTATE INVESTING is going for you and what can make it better!

Looking forward to responses!! Thanks!!!