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Thoughts on the stock market and

So, here is a couple questions for all you smart folk:

I'm 31, and I need to start planning for my future. I currenly own a townhome, two small businesses, a car, etc. Here is my big question that I keep tossinb back and forth:

I'm not sure if I should plan my retirement mostly through 401K's/IRA's/stocks or try to keep that to a third of my retirement and turn the townhome into a rental and use that income to buy more rental properties (1/3rd), continue to grow my businesses and open more locations to sell off someday (1/3rd) and traditional methods for the other 1/3rd.

The plan for the townhome is to rent it out, every penny made off that goes into an account and when that number gets high enough, use that cash to purchase a second rental property, then repeat. I figured if I did this, in 30 years if I had 10 properties with zero debt and $1000 a month from each one, that would be $10,000 a month in income.

The businesses are pretty stable as well. I currently have two and plan to have them both paid off in 5 years. At that point, do the same thing with the businesses as the house plan. Buy another, then use the $$$ to pay it down quickly, then open/buy another. I think 5 would be about as hard as I would want to work. Then, when the time came, sell them off and use the money to fund retirement.

Am I crazy? Am I putting too much faith in real estate? The market? My businesses?

Thanks.
 
One piece of advice, green. Don't fall in love with rental properties.. they're not bad, can be very good, but remember this; You don't make your money on real estate when you sell it.. you make it when you buy it.

Put MUCH more emphasis on buying low than anything else, including rents.
 
One piece of advice, green. Don't fall in love with rental properties.. they're not bad, can be very good, but remember this; You don't make your money on real estate when you sell it.. you make it when you buy it.

Put MUCH more emphasis on buying low than anything else, including rents.

question.. what are your thoughts on storage units? always thought that might be good investment. pay a ****load upfront, but then maintenance and operation costs are relatively minimal. only have to worry about maintaining high occupancy. good idea? bad idea?
 
question.. what are your thoughts on storage units? always thought that might be good investment. pay a ****load upfront, but then maintenance and operation costs are relatively minimal. only have to worry about maintaining high occupancy. good idea? bad idea?

Just depends on the demand in the target area. I know about a dozen guys that have facilities and most love it. As you said, low maintenance, nice passive venture, and good income to boot. Those that don't like it built in an area that was already saturated. Duh.

I have a completely other theory, but it's too complicated to discuss here.. but in a nutshell, I like to buy properties that I can buy, flip for profit, and maintain a mgmt arrangement that also guarantees me an evergreen income. Example: Buy a condominium complex for X.. sell off the condos for X+, but create CC&R's that allow for an overnight and long-term rental plan naming my company as the mgmt company and MORE importantly the exclusive rental agent. I invest the money, get a nice ROI from the subsequent sale of the individual units, and then mega boost that original ROI through 10+ years of mgmt fees. Now, this works better for me than most, because my forte is knowing how to get things SOLD.. I'm the best at that.
 
Why not buy em in a roth and never pay a dime on the rental income?

It's a good idea but you're limited in your purchasing power because the rental from properties purchased through a Roth are still taxed if monies were borrowed to complete the transaction.
 
You know, I have up to this point not done any day trading... you make it seem like something that is worthwhile. ;)
 
I have yet to play the stock market or crypto beyond buying and holding via index funds but just last week I was talking to my wife about doing a little playing around. Now the Warren Buffett quote "be fearful when others are greedy and greedy when others are fearful" is coming to mind. When will people be fearful enough for me to make my great entrance to individual stocks?
 
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