For example; If you need to force 20% equity on a 100k home VS forcing 20% on a 200k home that is a major difference.

Non professional practices will normally result in major financial losses.

Next there needs to be some research on possible capital gains, and to see if your grandmother can use the primary home exemption to avoid paying taxes on the profit  up to $250K if single, and $500K for married. 

Target Refinance Property Value: $180,00075% LTV : $135,000Anticipated all in costs + Loan Balance of $95k: $122,607.42“SHOULD” get all of my money back ($27,607.42) in addition to some profit depending on the closing of the refinance.

If I can't close on time I stand to lose out on the $2,500 but if it goes through I could make a potential profit of $40-50K, maybe more.  

Why does the majority of wholesalers "downplay" that they are not the final buyer?

This seems the best engine to get into buy and hold.While my credit score is in good shape at 793, the down payment is the major roadblock.  

We have some experience with SFH's and duplex properties but have not done anything outside of residential until now.This property we are looking at has major roof issues that currently make it unsafe, but the rest of the structure looks like its in decent condition, I mean its an old brick building.

What are some major questions I should ask.

Just trying to get some ideas for proven successful tactics for making land a profitable investment.