I work full-time but also own a couple small businesses generating some additional cash flow on the side.

If you are looking to buy in a year from now, you can do a lot between now and then to generate cash. 

If it's a sale or long term hold you want to determine the revenues you can generate and back into the project that way.

I'll keep that in mind, if I find my searches aren't generating what I'm looking for.Thanks for the encouragement and best of luck!

No self sufficiency rule for 2 unit.Since you are in a high cost of living area, you will definitely get the biggest bang for your buck doing a low money down house hack using fha or VA loan (if you qualify) than putting 20% down on a random out of state market that you may not know very well.Best of luck!

@ Ryan Fox  I'm looking to either a) Put a truck parking lot on a portion of the land to generate some income or  b) Lease the land to someone else with bright ideas,  Land is zoned industrial.

He suggested the following as rules of thumb:Multifamily $100/month/unitSingle Family $200/monthCash on cash return 10-12% (annual cash flow/total cash invested)Equity of at least 25% (property value-debt)Total return over 5-10 years 15% (double the stock market) as measured by (total profit/total cash invested)/number of years1 or 2% rule-- rental income generated/purchase price = at least 1% or 2%Even if you know all these things, the webinar was a good refresher.

Those super expensive skyscrapers won't go to waste...their owners would never let it and millions in tax dollars those buildings generate are vital to city services.

I have a property that generates a 20% CoC currently that I bought 2 years ago.

What else is multiple streams of income, opportunity to build a team and generate income from the sales of your team members, the opportunity to sell the properties you don't want to flip yourself to someone else who might.