You want to consider the quality of tenants you get and being in a central area means people can get to their jobs / school conveniently.

Current rents and building quality needs work, total rent income is around 5k/month, parcel is quite big 14k sqft.

@Celine Li Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Is the tenant quality good? 

What qualifications do you believe you possess that would make you a good candidate to advise others on the quality, safety and performance of potential investments?

Some of their resources are more pricey than others but they are all quality.

ADUs can significantly enhance your property's value by adding living space that can be used for rental income or as additional living quarters for family members.The increase in value from an ADU can vary widely depending on several factors such as the size, quality, and functionality of the ADU, as well as its integration with the main property.

I wonder if rent control laws will be easing anytime soon in this city - other than capping rent prices, I don't think they do anything to help improve the quality of rentals.

Like you mentioned , the prices are going down because a lot of people thought you could just buy a property and slap it on airbnb , expecting it to rent well without doing improvements , not realizing that the market would be overstaturated with " C and D " quality properties ( A+ are the properties i'm speaking of)I'm seeing that you can buy those type properties( A+ potential) that have simply been under utilized and 1.

I now currently work for a PM in Milwaukee that has the same focus as you, to provide quality property management and we have prioritized quality over quantity as we have grown our business.