We just had this done on a house in UH.Just my .02 based on recent experience with an owner turned landlord that can not sell Good luck

Different tax base use.

I'm trying my best to cover all my bases, but getting over charged $27K from what I expected has gave me some caution but not enough for me to give up if this property comes back onto the market again.

In Chicago, the landlord tenant ordinance is very strict, specifically around security deposits and many landlords have lost judgements based on technicalities.

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.