If the sender selects "sending money to family and friends" there is a smaller charge.

With all the hoops one must jump through to get their license, I am finally to the point where I need to select a broker.

The reason is that the price range you outlined is likely to put you in C or worse areas and those can be very difficult to manage effectively. 

You should use either LLC’s (the old and expensive way) or a Series LLC (the new and more cost/time effective way).

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Also how does this effect our landlord insurance?

Everyone kept saying it is hard to comp bc of the second house on the property, but the town considers it single family since the cottage was built before multi family zoning laws were in effect.

Maybe it wouldn't bother me so much if I didn't have to pay taxes on the Martha Stewart effect and those handles cost a more reasonable buck-fifty or so each.

I am trying to select a market to invest in and I am looking for advice on how to go about researching a market. 

Through automation we are able to make our operations more cost effective and with the rise of folksonomy and the sharing economy, smaller scale operations are now able to compete on a marketing level with legacy name marks.