Most distressed Pitman properties I've walked have had deterioration of the walls of foundation or of the load baring structures.

The first thing you migh need to do is walk your existing property and identify every single existing room with exact or near exact measurements noting in particular walls as some can exist as load bearing walls, important structural members for the exisiting structure, Make a scaled down drawing of the exisiting .Use for example 1/4 inch equals to 1 foot.

The point being is the you have to want it more than anyone else, but make good deals not simply load yourself up with properties that will not prove to profitable for you. 

Which should I give more weight to as one guy job is to identify risk and the other is to actually get the work completed? 

You are not trying to load yourself up with properties.

Are you on a septic that can handle that load?

The following estimates should be included: vacancy, maintenance, cap expense (level loaded across all months), miscellaneous. 

I'm also looking at the calendar of events for the local area to front-load guests who may visit for specific reasons.  

If they have some crappy lender and another offer has a good lender, that adds weight to or takes weight away from the offer. 

I need the leverage that comes with high cash flow properties to be able to expand and build.If early on I would have shot my load into 1 property w/ little leverage, I'd have been screwed.