Keep in mind that many companies have salespersons to do their estimates (and @Nicole W. and @Russell Naylor) and may not ever step foot on the roof (if only for insurance reasons).Unless there is something pretty unique, estimating roof work is fairly simple.  

Nina is passionate about real estate as one of the best investments over time and feels very fortunate to be living and working in this city of a culturally diverse population, unique architectural beauty, breathtaking historical buildings and museums, and astounding lifestyles. 

As James Martin wrote above, your target price range is challenging, but it's doable with the right team.  

At one time there were more PHD's in tiny Brevard County than anywhere except Silicon Valley (unsure if this is still true, but I know many are still there).Fort Myers is unique in that it is one of the top five growth markets in the United States, AND deals can still be found on the inexpensive end.

That is the challenge of self management The is a huge obstacle to overcome.  

Look them in the eye when you ask your challenging questions.

what a challenge for wholesalers.title search before putting house under contract or not?

If so, the seller financing method such as what Account Closed brings up a good idea about 1031s.There are other, more unique and creative solutions.

I have liquidity from the previous business to invest and hopefully kick start this endeavor.Biggest challenge - I don't know this industry, I am coming from a completely opposite industry in the technology field.What I have, I think, in my favor, are colleagues from the RE industry with experience in both traditional RE sales (agent/buy/sell) but also experience in the REI side (one owning about 70+ properties and the other owning about 25 properties, both using their properties for passive cashflow)With an engineering/analytical background, my greatest fear right now is the unknown and I am trying to shore up that experience through reading and listening to others, but as I have already discovered, its like taking a drink from the fire hose - way more knowledge than I can consume in a short period of time.Questions I would pose to anyone interesting in providing some feedback -- Best way to look for that first opportunity?  

I plan on buying 2-3 properties, so it's going to be a challenge!