Given the age of the roof, is it necessary to get this fixed?

I have never heard of the title company taking payment from the actual credit card but I don't know everything :) The problem with the "cash advance" feature of the card is that this limit is generally capped at a much lower amount than the actual credit limit thus limiting your full potential to cash.

If issues were going on at my property I would like to know about it and have a chance to fix it first. 

I usually head to the house once a quarter to check up on things and fix anything that might need to be repaired (and of course have some fun up there).

I have found a good amount of info on what that would look like with flips, but not for STRs.  

In that environment buying in the hood becomes very tempting, but that little bit of cash flow comes with a huge cost in headaches, the probability of property damage (things like a charcoal grill in the living room) and long term you might just be treading water.Average net cash flow is probably around $200 per door after you have stabilized the property, so you need a few units before it amounts to something.

The issue with our loan would be that there is no collateral since our loan amount would be more than the land value itself if anything were to happen.

Give them a specific amount of time to clean it up or face a penalty. 24 hours should be more than sufficient.

One observation in working with higher loan amount borrowers and lenders recently is that rates can often be LOWER than conventional loan amounts. 

Marion oaks has become harder to rent because of the amount of competition but I like it for long term because that is the side of town with the most growth.