If this is a wooden structure, you may want to submit a claim to your insurance if the damage is a long term spread of wood rot.

Are they old wooden windows that are in good shape or need a ton of paint and TLC?

If you have a giant, old, wooden house you will need to budget for a lot of ongoing maintenance that will be painstaking to do yourself and expensive to pay for. 

You're just racking up a bunch of LLC fees yearly and you have to separately file Tax returns for each LLC which also adds up. 

., bikes, racks.

We live in an area where the summers get over 100 degrees and you can rack up a large bill running the AC all the time.  

Its just outside a family beach resort and Ive been racking my brain on how I can operate the building either seasonally or short term and still utilize property management without operating as a motel where I have to be available 24/7. 

A water stain on a wooden table is neglect or abuse, not ordinary wear.

You could rack up expenses really quickly with this method.

The best part is that you pay all of your bills on your credit card, rack up the rewards then other people pay you back the balance!