They have been featured on BP podcasts before and work a lot with investors in the area across multiple types of investments (SFR's - multifamily).

I recently tried the Cozy/Apartments.com solution but it seemed to be missing a lot of features. 

I'll try to determine if it's better or worse than my rental in terms of condition and features.

Rentals in your target range will have a pretty common set of features.

Then out of the pool of listings that are the same size and have similar features, I do exactly what you are doing and look at listing photos!

In the end, we will all be fine as @Brie Schmidt mentioned and in my opinion it will make the city slightly more attractive for local investors since not having the land lord tenant ordinance was one of the attractive feature about operating in the suburbs. 

Additionally, many of the antique houses have quirky features including, but not limited to, box outs for heating/ducting, chopped up rooms to accommodate bathrooms and other modern conveniences, small closets, knee walls, lower ceiling height, etc.

I imagine you can get a $200-$300 hundred more for sure but what this feature does is get your place rented faster and tenants stay longer which in the end of if you have 2 less turnover overs in a 10 year period then you pick up a chunk of money there in addition to the few hundred more.  

I was thinking Quickbooks which is $30/month for the features I need.

Great way to try it out, and not loose out on future features for free up to 75 doors. 150 doors for $9/month is a steal, and 500 doors for $35/month with quickbooks integration is well worth it, if you had that many doors to manage.If you compare to what large property managers use - Appfolio runs a minimum of $250/month or $1.25/door.