Have GCs give quote on rehab (use home inspection as a base for SOW)7. 

Its all mostly based off  of your income  

Thus far based on browsing on loopnet.com, Tampa, Florida and Hagerstown, MA appear to have properties available that fit my budget and desired unit size (4-10 units).

Some relatively simple formulas can make it almost automatic and will suit your needs.If you want to get additional features support, my personal favorite cloud based accounting platform is Xero, but also Quickbooks is extremely popular with lots of customization options.Let me know if you have any other questions.

Is it an estimate based on date of conveyance and recording?

Unless you are a qualified inspector and are certain of the condition based on your indepth inspection.

I am also looking for an investor based real estate agent that knows these areas and has experience helping investors or has invested themselves.

Based upon my experience, a buyer in a similar circumstance as you will be signing an extension and closing whenever the bank is ready. 

Therefore, what investors need to do TODAY, is make decisions on based on today's prices, returns, and future prospects (relative to PV).Hope that made sense.Continued success!

Get with a Contractor and a Real Estate agent that you can trust. get the contractor to bid on the rehab in order for you to understand what it takes for that property to come up to actual value, get comps from the real estate agent to understand what the property is worth, make an offer based on those numbers and move the property to an investor.