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Scotts book on estimating rehab costs arriving today, I'll also check out his book on flipping houses.

I think you may struggle to get a contractor to check out a property before you are under contract unless you pay a fee.

I'll checkout Bluebeam. 

If you are considering doing a flip/rehab check out the lead laws for Worc and MA which are stricter than CT.

Check out what others are renting on AirBNB in the area and make sure that your property will get the rates you need to cover your bills and still make a small profit.

We use Uhaul software, but check out Storedge. 

You may want to check out the radius of those areas such as Harambee or Halyard Park which is still slightly rough but competitively priced although rising....radius of Washington Heights (zip codes 53208 and 53210 are big duplex investor areas).

You should check out Columbus Ohio. 

If you are interested in the wholesaling side of things, check out Ronnie Reese on "Indy Investor Podcast", he has been working on putting together some meet-ups.