I know the capital gains tax on investments shorter than 1 year have at least 35%+ tax.I try to tell people to beat the tax with volume, the 1031 exchange program can be a pain with their guidelines and process. 

I previously transitioned away from a corporate role so I feel your pain lol. 

It's a pain.

I self manage my portfolio while having a demanding full time job so that's always my pain point. 

Nothing in Tampa, although I did consider investing there in recent years.One pain point is going to be doing a remote closing if you want to do that.For Florida you will need wet signed papers for part of the transaction (title transfer), so you'll need to get a US notarization from the embassy, and then physically mail stuff to the US (overnight air mail).

I deal with development opportunities where I can and synergies between local businesses.Then I have my operations manager who handles most of the day-to-day management of the properties, and they manage some of our contractors and managers.Our model is a little different than large parks because we have regional managers that cover multiple communities vs a single one.The pain point right now is mainly having consistently qualified contractors and filling vacant spaces as quickly as we can.

A painful learning experience, to say the least. 

well i lived through it.. painful as it was.Gap lending is far to risky for almost anyone end of story.. totally agree.the only time it works is with some decent cross collateral and or you have a substantial relationship with the client and have done LOTS of deals with them for many years. 

Not to mention the paperwork pain involved with each claim Any thoughts on just not having any insurance at all, or just some sort of liability and really high deductible ?

We worked out a buyout from it but it was painful.