These plans come in IRA and 401k formats and will allow you to operate out of a bank account of your choosing and eliminate all the 3rd party processing of a trust company serving as custodian.The goal of flipping houses may also have tax consequences inside an IRA, since this is viewed as conducting a business activity.  

There is always a trade off of cashflow vs. liquidity and most properties in NOVA can be sold in a few weeks.DC/Nova is not an entry level market and you have to be VERY creative if you are working with limited cashflow.  

Also, for me an acceptable cash flow depends on the risk trade-off of what I'm getting into.

That way the tenant has to deal with you if they want to buy the property.A seller who is willing to sell an option on a property is willing to trade getting top dollar to reduce hassle.There definitely are risks in these transactions, but I think they are different that what you have identified.

In addition, keep in mind that buying real estate always has trade offs.

Originally posted by @Robert Lenfestey:The tax consequence of any particular entity structure is likely to determine which structure makes sense for you personally.  

Cash flow is very hard to find in NYC -- maybe deep out in Queens or the Bronx, but the trade-off is that the areas are not as likely to appreciate as quickly.

Thanks for the added advice, I do like the idea of splitting up the money and putting it in different outlets, and getting a duplex or something and learn the trade for a year.

He wants to trade his shed in return for staying.  

Just as I can sound very negative about the possible dire consequences for anyone thinking they've just found a magic cash machine by buying in the lowest priced areas here in MKE, I think the flip side of that is that a landlord who gets a great rep with both the residents AND the city as a decent landlord could have all sorts of great opportunities fall into their laps over and over again!