I have a break-lease fee equal to 2 months' rent in the ones I self-manage, which actually deterred at least one tenant from leaving months early, but I will also work with them if they have been great tenants and allow me to advertise and find qualified replacements to take over when they leave.  

We tell our prospective tenant/buyers (and we always refer to them as buyers) that their "down payment" goes 100% towards their purchase of the property.  

I'm scared the price might be a big turnoff for prospective tenants.

Any prospective buyers would have the same questions I'm having, and all I'd be able to do is shrug and say "I dunno, it's been there for 60 years!" 

This thread is confirming my suspicions that I would most likely come across as a pest looking to waste the valuable time of a professional, with nothing more than the prospect of possibly funneling some business their way, IF several things fall neatly into place.

Lots of prospects will call, ask about property, I pre-screen over the phone, and they either hang up on me or not show up for showing, or if they show up and after I give them application and they never come back with it.... 

Notwithstanding, SEP contributions are voluntary and discretionary (depending on your structure), so a banker/lender should recognize that, prospectively, such contributions are not necessary operating expenses.The upshot of all this is that you should reach out to your mortgage broker and lender ahead of time.

My clients hire me to do this type of research ahead of prospective renovations & additions. 

But if you're willing to give up some cash flow for the prospect of greater appreciation, you can come out ahead in the end because the increased taxes could be more than offset by appreciation.

Prospective tenants walk in and say "Whoaw this place looks great I want it....but don't know why"... because it's slightly different from all the other units in the regional market.