However, if one could pick it up for say 10 cents on the dollar, could be a gamble willing to take.  

Let alone accurately quote a renovation

Also in a situation like this, what would be the most accurate appraisal to help me determine the value: a fee simple vs leased fee or something else entirely?

When it comes to a standard SFH rental, I have a fixed price for rent for at least a year with a tenant and a vacancy % (that I get from my property manager) that is fairly accurate. 

For example, you may want to have a roofing inspector give you an estimate (if not already) for a more accurate budget or periodically check on the furnaces/coolers to more accurately anticipate that expense.

But isnt that more of a speculation/gamble as opposed to tangible money?

First of all, I am still new to this forum and REI, and I am doing my own research about REI One of many questions that I have in REI is how do you accurately estimate the property tax that you might potentially buy?  

It's a little bit of a gamble, but if it's a relatively small volume then you have more possibilities.Is there anything stupid about this strategy?

Most wholesalers numbers aren’t accurate.

When another buyer owns the building however a single property policy or just a few buildings will likely be much higher.It's important to tell accurate info when filling out insurance form for a quote.