My question is do I go forward with purchasing the property and deal with the higher insurance and potential hazard or is it smarter to walk away?

To invest out of state successfully, focus on building a strong local team (agent, PM, contractors), automating deal analysis, and using contingencies to protect yourself.

For the proceeds I have to pay seller I would have to issue him a 1099 right?

And must be pretty significant unreported income if it would have caused $45k in state tax liability.You advised your client to wait past the expiration of state statute.

The US Government and the States have but one way to deal with this, taxes.

Working to systemize this business to run efficiently with future limited supervision to then take the cashflow/profits to continue investing in building our long term rental portfolio as well as invest in other business endeavors.

Self-managing is definitely the way to go!

In your case, you are probably better off buying a break-even deal in Tampa then a deal with $200 cash flow OOS.

If the seller already has an agent, the agent is his/her legal representative so it's better to deal with the agent directly than the seller.

Following as I deal with STR in the lake region.