What are your biggest challenges as a new real estate investor?

I've been running a vacation rental operation in South Florida for the past 7 years, helping owners drive revenue. 

Poor insulation and single pane windows will raise that cost to run the furnace quite a bit so you might want to see where the break point is for upgrading.The biggest issue is power outages in the winter.

Good luck with it.A couple thoughts on your situation:-- When I'm looking at AirDNA for our Colorado STR investors, I don't care about occupancy and daily rates for STRs as much as gross revenue.

As a PM and a fiduciary to my clients I use a more complex software than most self managers use and also employ a live revenue manager to scan my local area. 

ThTs my biggest piece of advice.

However, the previous landlord permitted them to take over an additional 3,000 square feet on the second floor, which is now filled with inventory and unusable for other purposes.While this tenant has been reliable and has a long-standing relationship with the property, their occupancy of this extra space is limiting our ability to maximize rental revenue.

The biggest qualifying factor is positive cashflow.

The biggest obstacle I'm encountering now is the making up the initial down payment.

I find that two of the biggest mistakes are in the manner in which you ask for the money (there is a good way and a not so good way) and not having enough knowledge on the subject and the proper info on the presentation of the deal itself.When I need to fund I deal, I am not asking for money, I am offering a legitimate and alternative opportunity for others to make money.