There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

Florida scares me with insurance issues and constant threat of hurricane damage.

What's the most effective means of dealing with this issue?

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.

Good news is our land is where all of the next-door houses are (free houses, I think legal issues). 

The only issue we have run into is the prices and bidding wars.Every single home we have looked at for personal use or an investment seems to have 5+ offers and go MUCH over asking.We are currently looking at Bay Park / Clairemont / Carlsbad / Oceanside. 

I told him I was having these issues & he just told me to keep trying.

I was able to get 13,000 of them to opt in to receiving a monthly newsletter we issue, and as preciously stated results are 100s of deals or loan requests per year.  

My market also has this issue but I suspect less than Florida but my umbrella cost doubled last year.- as yet unknown impact from required structural inspections (bill 154).

However, you may not need to do this if you can discuss the issue with previous landlords.