I am keen on finding out whether this market is a good starting point if I wish to develop a small portfolio of say 5 rental properties over the next 5 years. 

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

I am over in Pinellas County, FL and we just hit an all time high for tourism.

The Assessments levied by the Association shall be used exclusively for payment of Common Expenses including, without limitation (i) the upkeep, maintenance and improvement of the Common Areas and other maintenance obligations set forth in Sections 10.1 and 10.3 below; (ii) maintenance, repair, replacement, and operation of rights-of-way and easements within or immediately adjacent to the Project (e.g. landscaping and sidewalks within the right-of-way of adjoining streets) to the extent that such actions are required by government entities or deemed appropriate by the Board, (iii) promoting the recreation, health, safety and welfare of the Owners and other lawful occupants of Lots within the Property, (iv) payment of property taxes for the Common Area; (v) insurance premiums; (vi) legal and accounting fees; (vii) management fees; (viii) charges for utilities and other services provided to the Common Area by the Association, if any, and for all utility charges paid or incurred by the City and reimbursed by the Association for street lights in the Common Area; (ix) costs to maintain the entrance features, including any electricity, landscaping and irrigation expenses associated therewith; (x) the performance and exercise by the Association of its rights, duties and obligations under the Project Documents, and (xi) maintaining any Stormwater Control Facilities located on portions of Common Areas to the standard required by the governmental entity or agency having jurisdiction over such areas.

Is it difficult if I purchase a property in my name and then I want to transfer the mortgage over to the LLC will my mortgage company allow that?

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

I'm very happy I stepped into this market, and will continue to grow it.

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

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.