Poker Win: Should I invest now or save and wait?

[Nathan J Trenkamp]

Hello, 

Recently, I won some money at a regional poker tournament ($88,000) (Ace/Jack is my friend). I have yet to pay the taxes on it, but all of it is still in a preferred savings account. Along with other cash savings, I have roughly $100k to invest at the moment. 

I know I should pay the taxes right away, but wanted feedback from more experienced people. Does the old saying "A bird in the hand is worth two in the bush apply in this case" Should I use as much money as I can now, pay a little taxes, like half, than go and invest in a multiplex? 

I'm really looking to invest in a plex. I'm not entirely new to the real estate investing game. I currently own a townhouse, 1 triplex, and 5 single family home rentals with my cousin. We bootstrapped the single family homes together, but we own 50/50 share in the 5 homes. 

I'd really like to put this money to use, but I know the market is red hot right now for sellers. Should I hold tight and wait for the market to cool down or should I look now and make my money work now? 

The Triplex I recently purchased, I used a HELOC as the down payment which came from the equity in my townhouse. Should I pay off the HELOC?

Any suggestions or comments would be helpful. In return, be glad to offer up any poker advice :) 

Thanks