The IRA money is what it is, and is treated differently than after-tax money in all investment scenarios both in and out of the stock market.

house hacking is a great way to start...You keep a close eye on your tenant, you live mortgage free, someone else subsidizes your equity position, and you get a second rental when you decide to move on to a new house.Also you in theory get to stock pile your cash you would have paid in rent/mortgage.

Do you stop investing in a 401k because the stock market is near the highest it has ever been?

I think I'll buy Home Depot cabinets in the future, even though they are more expensive, because they're in stock instead of having to wait for them to come in. 

This afternoon my wife and I have a meeting with the  financial adviser who manages our stock and bond portfolios, and one of the key areas of discussion (for us) will be use of self-directed Roth IRAs.  

It's like in that case you are asking them to grow this company to a huge success but giving nothing but the same paycheck in return.This is why companies have stocks, bonuses, etc.

When I did this on my primary home 20 years ago I would simply look at the amortization schedule, and pay the next principle payment.

I can get the basic principle of taking your annual rents and subtracting insurance, property taxes, expenses, etc. 

I realize that you are not impressed with the housing stock/deals in your immediate vicinity and neither enthusiastic about going out of state as I did.You might want to look for a small multifamily unit within a 5-25 mile radius of your current home. 

Now that i am out and going to school i have more than enough time to study about real estate.I am also into stock mostly microcaps so any info would help especially how to read a level 2.