Being able to use real estate to offset taxable income requires some sort of participation on his end.If he wants you to be the boots on the ground, it will likely be hard for him to reduce his taxable income.

Since you're in Destin, you might want to check with local firms that have experience with STR-heavy communities, as they’ll be familiar with the risks and requirements.

Some lenders require a longer seasoning period before allowing a cash-out refi.

Then I’d avoid capital gains tax in Massachusetts?

So I pay it, and every few weeks when the stars align and I have no work meetings at the time, I join, listen to other people's questions and Peter's answers and that's it.At least after reading your post I feel better knowing that some clever tactics were practiced to get me into this and not that I was easily fooled.I would be happy to share info if yiu think it will help others make decisions and avoid shortcomings, and I would appreciate it if you have some advice that might help me get out of this situation.Thank you! 

"variable income" will require a 2 year average of income/ earnings to qualify. 

I recommend you send notice earlier than required and by multiple avenues to verify receipt.

This is not even close to the documents required for a properly drafted loan.

Quote from @Tim Baldwin: @Nathan Gesner, that form should not be used, as it provides for 60 days notice to terminate a month-to-month tenancy, which FS 83.57 only requires 30 days.It was a ten-second search for an example.

You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.4.