I think that the best time to buy investment property when you aren't 100% convinced that you are getting a fantastic deal (which, by the way is exactly what you are doing - by keeping the first property as an investment instead of selling it to pay the downpayment for the new one, you are essentially buying an investment property) is when you are financially prepared to make that purchase. 

My partner and I currently own what essentially amounts to a number of rental properties, a construction company, and a property management company all under 1 LLC.  

Working full-time for the USPS, you're essentially going through neighborhoods and looking at properties.

Essentially lots of good debate about whether you need an attorney and things like LLC or insurance.  

Work your numbers off the low number for safety, and if you sell for the high number, be very happy.I personally would not buy this property for more than 53,000.

@Keith Dowdy there are essentially 3 investor types of meetings that happen consistently in Raleigh.

The problem with MLS listed properties (REO's, short sales) is that essentially everyone has access to them so competition is fierce.

If you are really in a seller's market, you should be able to negotiate a cheaper real estate fee - that will usually tell you whether you are truly in a seller's market; whether or not a realtor is willing to take 4%, 5%, because it will essentially be a no-work sale. 

If you purchase a property with a great deal of equity, than you can essentially pull out the money from your initial investment of purchase price plus closing costs, with delayed financing immediately.

It's a life-safety issue.