Having said that there are a couple of approaches that may help you;The strictly analytical approach would be to look at ROI; what is the return of each of your options.

We are looking for a real estate investment agent who is analytical, familiar with Indianapolis submarkets and does property investment themselves. 

They are peices of the analytical puzzle sure but in the end they can be really more of an emotional reason for a decision.  

I plan on looking at our next home (single or multi-family) analytically to buy it right, so when I move again, I'll be happy with the outcome and cash flow and can focus on building a portfolio and part-time business that I can be proud of and maybe transition to after life on the move!

Looking for a spreadsheet or other tool to help me evaluate when to buy more properties versus paying down the ones already in my portfolio. I am a new investor and am working to determine the optimal strategy for rep...

I was hoping to  chat with someone who has actually used these types of remote data analytic real estate investment services. 

Another IT guy - it must have something to do with our analytical brains - i seem to hear about a fair amount of IT turned REI's!

My potential solutions to the 3 issues are 1) The internet (Trulia, Zillow, Rent-o-meter, etc.)   2) Touring the competition (similar properties) Asking them about their rents and occupancy3) Talking to the current property manager and other local property managers 4) Reaching out to local real estate brokers about the rental listings and the property in general 5) Trying to connect with local investors/landlords thru BP and REIA meets 6) Asking the current owner of the property for the last 3 years of financials before its under contract (probably wont be willing but its worth a shot)  7) Reaching out to the big commercial brokers like CBRE who have closed transactions in the surrounding areas8) Somehow get REIS, which is an real estate data and analytic firm to "demo" their platform to obtain more info on the market As for now these are my potential solutions that I am working on but I would like the community to help me find other solutions or provide some advise. 

Can anyone point me in the direction of analytics showing the appreciation of similar sized condos and coops in the New York area for the past 30-50 years?  

The above based on county-level valuation metrics I compute in-house for my own multifamily investment/data analytics endeavors.