If you dont have a contractor lined up before you buy anything , you will be waiting months before you can start work just looking for a contractor . 

Getting multiple contractors involved will be your best bet to get a reliable estimate, though you need to come up with a scope of work.

The Prosper Construction team redeveloped this building back to it's original glory.

You have to get contractor bids to qualify, but ten you can do the work yourself after closing and build sweat-equity.2) Be very picky about the next property you buy and make a bunch of lowball offers to find a motivated seller, willing to sell under market.

I did this 10 years ago and pursued a heavy renovation with contractor/tenant.

Not only would you benefit from having a partner's input on the deal, but you would also have an experienced individual to work alongside with as you navigate the project.It's also important to make sure you have identified your "team" ie; contractors / realtors / lenders / insurance agents / title company / etc. 

I wish I had known more about landscaping at the time, and didn't go cheap when it came to contractors.

This is something a qualified contractor can easily resolve.

I'm a carpenter / contractor by trade, and I've done a few major whole-house renovations of personal homes over the last decade or so.  

If one is not accustomed to working with contractors, then your expectations are probably unrealistic.