With real estate the people that fail are the ones that never pull the trigger. 

This  does not trigger the same flags with traditional lenders, and when established correctly can keep your name anonymous from public records. 

I also agree that I need to get some estimates from the contractor before pulling the trigger.

Finally, I decided that there was only so much reading I could do and that I'd actually have to pull the trigger at some point to get some real hands-on education.  

I've heard of people here transferring ownership to an LLC after closing, but that could trigger a due on sale clause with the lender since you purchased the property as an individual not a business. 

You want to check with the insurance company before pulling the trigger on this for sure.

And if you can, and you've really done your due diligence, pull the trigger on it!

Good to go as long as you are not being negligent.The LLC protection may or may not be worth anything and may or may not provide any greater risk reduction than is added by triggering the due on sale clause.

A “flip” (short term) by definition doesn’t qualify as an investment property so when you sell that flip it will trigger not only the tax due on the flip, but also on the deferred gain that you 1031’d into it.You can’t 1031 into a personal residence.  

I've asked about prepayment penalties, interest rates, interest only payments, closing costs, points, qualifications, etc but am unsure how to pull the trigger on one now.