It's a recognized destination globally with over 70M tourists a year.

Hi Dan,We do over at Lower.com - it is rare and we're a near National Lender.

If you are not willing to spend time on the island, put in sweat equity, then PR is not the best place for an RE investor. 

There are over 20+ active CPAs here in Biggerpockets assisting RE investors with their tax planning.

Was able to have the seller pay all closing cost and fees (over $25,000) How did you find this deal and how did you negotiate it?

There are schools all over, including Wilmington for sure. https://dpr.delaware.gov/ has all the details on schools and requirements, typically the schooling can be done online and then the test is done in person at a testing center. 

There is a safe harbor for you…it’s just 110% of prior year since you’re over the $150,000 AGI.You can also base on 90% of current year’s taxes to avoid the underpayment of estimated tax penalty.Keep in mind you can use Form 2210 along with your return to show the IRS how much income you earned by quarter and make your estimated tax payments accordingly.

If you don't want to spend and you know your target area, pull a better list from List Source and mail handwritten letters.

I will spend more time answering in detail.

Over the last year he has slowly slid to consistently being 2-3 months behind on his rent.