@Ashley MartinI know coming from a Realtor, this sounds like you need a good Realtor on your side! 

You need an agent who’s more than just a salesperson—someone who truly cares, understands your needs as an investor, and knows how to balance deductibles when to insure, and when it’s not worth the cost.

Also, consider partnering with experienced local investors or contractors to minimize risk while learning.Let me know if you’d like help with financing or any real estate questions along the way!

Also, they know things about where you are working...Keep in mind that your municipality will have codes and regulations as well that can be hidden costs. 

I also don't know if there is damage to the roof until I clear away the massive tree. 

Let me know if that makes sense or not.

Nothing wrong with it and I know for many, it is a great income producer.

If I am missing any information that could help our situation, let me know so I can include it in when talking to lenders.

Thus, if the owner of their Milw, Class D property replied without noting the above, he/she might say it only costs $1000, whereas the owner of the SF Class A property might say, $10k, but if I didn't know their location, property class type, if they used contractors, or did the work themselves, etc., then I would still have too wide of responses to be able to anticipate what the real costs might be for my particular situation, property, etc.For reference, my properties are in Class B areas of Milwaukee.

Therefore, you must take on all the property management tasks yourself.But rental property owners who are landlords know the job can be exceedingly time-consuming.