Commercial property usually allows the tenant to make improvements suitable for their business but you need to set limits, establish an approval process, and decide what happens to the improvements when the tenant leaves.You can get by treating it like a residential but I highly recommend you learn how to run a commercial property and get all the benefits of that investment.

Also there is a seasonality involved with March and April typically being our highest performers due to the events happening during that time.

As crazy as it is to see Philly on the list twice, the crazier part is how much room there still is for improvement.  

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

We'll keep the property in the family and use it as a rental, with capital improvements along the way.

A staged lease-reading followed by a Q and A is much more the kind of training and performance exercise you need in the landlord-tenant relationship.Of course, once you get up past a certain number of tenants, holding these kinds of formal lease-signings is going to get very hard to handle and/or you're going to get sick and tired of showing up.

Appraiser will of course see your purchase price and treat it as a data point, best way to overcome that is to hand him a before/after binder that includes all improvements you've done to the property etc. 

What is normally done, is it typical that they get paid regardless of their performance, or lack of performance?

The one that I'm sure I have a lot to improve on is managing contractors. 

Are you planning on trying to force equity by fixing it up and making improvements yourself?