FWIW, 20+ investors on one deal is a lot of people and relationships to manage, not to mention financials to prepare.  

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. 

I read the blog on 7 tips to prepare for and host an open house.

I definitely do not want to be stuck in the analysis paralysis zone, as I have done that before with other things and I know how that can kill momentum early.I do feel as though I need to be better prepared in order to create those relationships with a partner/private lender, though.

It definitely pays to have a relationship with a realtor be upfront/honest with them and be prepared to pay them for their time to provide their professional opinion on comps, rental value, the neighborhood,etc. or find someone through BP that might have access to MLS. 

Go to auction and be prepared to bid.  

Be prepared for a lower rent in your financial model.

Nice collection of nuggets in which i can prepare for even before having done it myself.Thanks @Jason Magee  for the double down.

Be prepared to get an updated appraisal.Best wishes.

Be prepared to have him make a hundred offers at a price to rent ratio that does work for you in order to find the one deal that will close.