But I appreciate that those who have found their footing in real estate and are doing it successfully want us newbies to understand it takes work and at least some capital.

That attorney should have creditor rights background in the state to understand what you can and cannot do. 

I'd like to understand which is the better option between these two and the reasoning behind it. 

And by DSCR loan, I'm thinking standard 30-year DSCR loan.

While many of these issues are important considerations and should not be ignored or overlooked, there are other more crucial criteria that you must question and evaluate first.The critical risk criteria that you must review and evaluate prior to making your final decision on which 1031 Exchange Qualified Intermediary to retain includes, but is not limited to, the following areas:Technical capability of the 1031 Exchange Qualified IntermediaryInternal processes and audit controls to safeguard your 1031 Exchange funds and assetsUse of Qualified Trust Accounts or Qualified Escrow AccountsDecision criteria and guidelines for investment of your 1031 Exchange fundsProtection from potential errors or omissions by the Qualified Intermediary (E&O Insurance) Protection from potential theft or embezzlement of 1031 Exchange funds (Fidelity Bond) An experienced and professional 1031 Exchange Qualified Intermediary will understand these concerns and should be happy to discuss these crucial issues with you.

For the historic district, I would just make sure that you fully understand what requires approval and what that process looks like.

So, you have to understand your customer as well as part of learning your market. 

I just did my first land deal, went to the builder for advice due to not understanding the process and how to price in that area.

If people want an area to build with understanding day 1 may not cash flow but in 10 years you will be in a really good spot the area I believe is perfect for that.

I understand that means paying the right professional for their services.