Don't put a high list price based on what you want, needs to be based on solds

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

High risk areas.  3.

If you are new to the business the most common issue is you're either locking up deals too high or you aren't finding attractive deals.

I agree with the other posters...25% down seems a bit high.

There was a news reporter at the sale and they interviewed the high bidder, who admitted that they had not seen the property, but were certain that they would be building their family home there. 

I'm in New York but the prices (at least downstate) are much too high for me to make my first deal so looking more upstate and out of state. 

This is a self directed RRSP or TFSA account that allows you to lend your money out to people with the backing of their mortgage for a high interest rate. 1st, 2nd, 3rd mortgages, down payments, refinances, flipping or renovation money.

Should I price the land 2 times above market value and offer a low interest rateORPrice the land at current market and use a very high rate?

There are numerous threads about sub to and many investors believe it is a high risk strategy (especially for seller) and believe buyers who use it “take advantage” of naive sellers.