I am one of the old guys who use to hand write an estimate in 3 columns, therefore I did not need a cumputer to do a property loss. However my first estimating program cost $350.00 one time charge in 1989 and I used it to write estimates for many years. Over the years I have used the DOS versions of all programs as well the windows versions. Now to the point of this post. I have switched to exactimate 25 as many of the vendors/carriers I seek work from require it for THEIR reasons, not mine. I am of the opine the training schools can give you a jump start on the production of paper going out the door, if you need to start work NOW.
If you just want to learn exactimate 25 and have plenty of time to learn..... this method is the one I now use and I will retain this navigation around in xactimate 25. Purchase a one month lease approx $150.00 and then purchase from xactimate the downloaded training program with several examples of claims. Print out the 250 page book(in the disk) and in 30 days of practice each day you should be on top of this game for less than $200.00 and no travel expense, plus you have the instruction book for life. I will say if you do not need this program Simsol and Power Claim can be learned by a person with average computer skills in several hours. MSB is more simple than xmate also. I do not have any experience with Simplistic Systems. I think both Simsol and PowerClaim will give you a free 30 day trial.
I still recommend the John D. Wagner book, House Framing @ Lowes $19.00 or Amazon for $8.00 which will give you a big jump start on 99% of new dwelling construction in the USA. This book is very easy to read, many charts, and if you can read you can build a house from this book. I do not think you will find estimating dwellings complicated if you do these suggestions.
You can find another person like yourself and send estimates back and forth to review etc. I will look over some off your work and critique it after you have spend about 200 hours of self training.