Hi Joshua,It sounds like you’ve got a solid situation—congrats on positioning yourself so well!

(Well it was all good info, but that is what I can focus on first!)

He says that the front door was damaged which he got repaired but there is some damage on the back side as well.

Absorb as much as you can, find the passion and you will be reaping the successes well before your 30th birthday.

Bought under value and currently adding a couple more homes and have brought two new tenants in as well What was the outcome?

Don't apologize, don't explain how the 'chosen' tenant was more qualified than they were, wish them well in their search.You're running a business and you've made a business decision. 

Lenders or investors who have short lock up periods but have years of experience feeding their business with new capital would give me more comfort but anyone who is just starting and is promising a rate of return or return of capital in a set period of time would be alarming because they very well could be reliant on fresh capital to make good on that promise and that usually ends poorly.

I currently own a successful short-term rental in Fort Lauderdale and have identified a new property nearby that I’m confident will perform well.

I am an investor and realtor here in Madison as well.

Having a commercial policy usually only covers property and liability, hence the reason for having the umbrella as well.