I would like to do some research on other rental properties before I set my priceComputer algorithms are good for studying a general market, maybe even a neighborhood, but they are terrible for evaluating a specific rental.

Does anyone have any insight into what these types of businesses are typically looking for in a partner and what I should be doing to make my space a good fit for them? 

@Mike Donovan I would recommend finding a local insurance broker to get the best rate to fit your needs.  

I wouldn’t move into the house because I currently own in a better neighborhood close by.Have they made it easier to get heloc’s for investment properties.

Chicago has plenty of opportunities for value-add projects, and I'd be happy to share some insights or introduce you to a few local investors I've worked with.Feel free to reach out if you want to talk strategy or specific neighborhoods!

Let's assume that the neighborhood is a C class and the median income of the city is greater than 3X of the market rent.Here are some of the considerations I've come up with so far:- Units are in need of renovation and capex is too high or not available- Unit quality is not the same as market - Seller is worried about losing tenants due to increase- Vacancy rates are high or filling units have been difficult- Rent increase would take multiple increases over multiple lease periods to get to market rate if seller is trying to retain the same tenant- Seller inherited property and just want to liquidate- Seller needs to liquidate quickly (financial burden, sickness, quick exit from land-lording)It seems like I might be missing a warning sign about a deal if they are selling with current rents that are under market; but again, this seems to be most of the properties I've underwritten.And in the same vein, what should I be worried about when purchasing a deal with under market rent with the intention of raising them after purchase. 

You have a natural advantage with other baseball players and providing them leases that fit their needs.Knowing a couple of others who have played minor league ball, your real estate strategy is going to be tricky because you will be very busy with baseball and it's travel. 

I want a real estate agent with a hustler's mentality, who knows the neighborhoods, studies appreciation and deal analysis already, understands short-term rentals, and is potentially looking to be a scalable partner with me.

This year, the State Legislature gave all counties the authority to change STR's laws however they see fit.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.