Even if the leaseback gets you a few dollars ahead in the present term, at the end of the agreement you still have a higher time airframe (which means lower re-sale value not to mention the fact that it was used as a trainer which also lowers resale value), a lot of abuse on the airframe and an overhaul to pay for - if you're lucky.
I would venture to say there are very, very few leasebacks that cover the maintenance reserve the all owners should be charging themselves.
For example for gas and oil our aircraft runs about $40-45/hr. But by the time you add in the other expenses (not including the maintenance reserve) it works out to about $140/hr.
The mantenance reserve on ours is quadrupled because it's a complex, multi engine aircraft. Money, in aviation, is like airspeed and drag it's all exponential and not simple doubling.
For instance, an overhaul on the O-320s we have run (on the cheap side) 18k and for a new Mellinium overhaul you're looking at probably more along the line of at least $22-25k. So, if you figure, for a 20k overhaul, your hourly reserve equates to (over a 2,000 TBO) roughly an extra $11/hr and that's on a single 160hp engine - and I'd be surprised if a trainer aircraft would make the recommended TBO. The more HP you add the higher the overhaul goes exponentially. In our case it's an additional minimum of $22/hr because we have two engines. And that overhaul reserve is not going to cover new avionics, wires, hoses, and the various multitude of other little things that must be paid for (like recurring ADs, new ADs, mag overhauls, starter replacements, vac pump replacements et., et.c ad nauseum).
On top of this add in the fact that you may not be able to use your own aircraft as much as you like (see R2F's post) and it's still a losing proposition because now you are not able to fly, or fly as much, and your aircraft is racking up time/abuse and
you aren't the one logging that time.
Now, if your sole purpose is to just buy aircraft and lease 'em out that's one thing but if you're looking to help pay for a personal aircraft I think it'd be better to go partners than go the leaseback route. Just my opinion.
And, yes, there are ALWAYS exceptions but in general I think the leaseback is great for an FBO but lousy for the aircraft owner.