That sounds like the logical path forward.

The next logical step is looking at the town next to me which is a college town.

The logic is that we collect rent no matter what for 12 months after signing the lease, understandable.

OP also specifically said Boston...not an entire county.If you want to throw numbers out, share the last 5, 10 years, or 20 years of year on year growth pertaining to Boston...and we'll have a logical discussion here.According to NAR’s findings, the median home price in the first quarter in the Boston-Cambridge-Newton area was $442,700.

But due to the “Magnolia Effect” and the counties approach to capitalize on it regardless of logic, these homes are now appraising much higher than they are probably worth.

As I continue to learn, I assume that finding a deal is the next logical step.

But for learning sake let's say -   For example, if he wants $10,000 now then I would offer along the lines of a $70,000 wraparound only for like 3-5 years (60,000 first mortgage with 10,000 wraparound mortgage over 5 years) vs if he wants nothing down then I would consider something like the above with an interest-only wrap around.I know that was a lot, and not super specific numbers, but I would definitely be willing to dive into those numbers deeper if that logic is sound. 

My logic is that unless home prices taper not buying now will only sacrifice C on C later so even if I'm not get 12%, 10 % now is better than 8% later.

Just keep in mind that motivated sellers don't make decisions based on logic.

It is logical if you think about it.