It comes down to the numbers.The concern with condos is you don't have control over the HOA dues or the exterior maintenance.

There exists some decent solutions for controlling a dehumidifier remotely.

Can you get direct control of the asset?

Rent Control is a two sided issue.

Just looking for some justification for not taking control of my life and taking action, seems like this should do the trick. 

While you can’t completely control who applies to live in your properties, you most definitely can find areas that are popular with students, young professionals, families, etc. 4) just as important as finding the property, you need to have an exit strategy in mind for the property.

The advantage of multifamily is the better control of valuation by the owner and the ease of operations since it's all localized.

You need to develop a Scope Of Work that is precise and then start getting prices for all the work.Once you have that magic number, then you will add that to the cost you pay for the house, along with any other fees or expenses...Then look at finished Comps (get a Realtor like @Chris Ayars said) and see if you will make any money......

Its a long game and if done with precision eventually you will have vast financial freedom.

There is no precise formula by which properties are placed into classes, but here is a breakdown of the most common classes, A, B and C:Class AThese properties represent the highest quality buildings in their market and area.