If you are a rookie and investing out of state, you are going to need an all star team.

Start by researching local regulations and working with an agent experienced in vacation rentals.

Exactly the reason to have an Architect on your team to join in on these conversations ESPECIALLY in existing renovations in older homes.

That's why it's important to be confident in your team so you feel like everyone is working together towards a common goal (good investment for you, agent gets paid for their support). 

At that point in time, we can just list the property and sell it. we have long-term capital gains rather than short-term capital gains, we would have probably experienced some appreciation during that time.

Many of those properties were build by my team for investors.

Tenants will push and try to get everything they can from their landlord.Seems you've done everything possible to be reasonable, yet the tenant is not satisified and wants more.As already stated, you are too much of a pushover, so the tenant is seeing how much farther they can push you.Highly advise you to find an experienced residential landlord-tenant attorney ASAP.

I want to get clarity on that from someone more experienced than I am.To answer your other question, the fund that Lee manages though is COGO Capital Investment.

Experience, and 2.) a team in place. 

However, I am unsure on how to go about finding the proper handyman/maintenance guy/management team to help run any out-of-state investments I make.