This is pretty much analysis paralysis, when you soak up so much info and keep reading and educating yourself, but NEVER take ACTION!!! 

Bureau of Labor Statistics and Bureau of Economic Analysis have good interactive data.

Run their errands, create their documents, load their listings in MLS, complete a market analysis, fetch their coffee, place signs and lockboxes, hold open houses, etc.

I am a Veteran myself, thank you for your service.

It has been often suggested here and elsewhere to pursue something that keeps a toe in the water of the working world, as it limits the downside risks, and could turn into a fruitful enterprise for post-retirement.At the request of a friend and BP associate, I've been asked to provide expert opinion and electrical analysis on residential properties that are either on the market, or recently sold through his brokerage, as there are many customers who want a deeper look at their electrical system, deeper than what a typical home inspector will do, but they are not ready to ask a contractor to come out and simply give a blank check to 'fix whatever's wrong' (famous last words).

Should I be viewing this process of evaluation as worst case scenario and run a good, better, best analysis and move forward if it makes sense on the better?  

Until you get established, your personal income is going to need to sustain the debt service on the rentals.

HOA includes water, insurance and maintenance.i have interested tenants ready for a 3 year lease lock in.The rent in the area is up to 2100-2200the seller is asking for 299000, i plan on offering 225k; i did the analysis on the basis that the property may be worth the seller's asking price. 

Does anyone know of any software that one could run a cash flow split analysis for a joint venture?

It is zoned Neighborhood Services (Mixed Use), which means it has other commercial uses.